Cushing & Dolan, P.C.Boston Estate Planning Lawyer | Massachusetts Tax Attorney | Wills & Trusts2026-06-12T05:51:39Zhttps://www.cushingdolan.com/feed/atom/WordPress/wp-content/uploads/sites/1404492/2024/09/cropped-favicon-cush-dolan-x-2-32x32.jpgOn Behalf of Cushing & Dolan, P.C.<![CDATA[The tax consequences of inherited IRAs]]>https://www.cushingdolan.com/?p=551482026-05-07T03:59:24Z2026-05-07T03:59:24ZInherited IRAs no longer function the way many families expect. For years, beneficiaries relied on the “stretch” strategy, taking small required distributions over their lifetime to minimize taxes. That approach has largely been replaced by a much stricter rule. Most non-spouse beneficiaries must now fully withdraw the account within ten years of the original owner’s death.
This shift changes inherited IRAs from a long-term planning tool into a short-term tax management challenge. The entire balance must be distributed within that ten-year window, and each withdrawal is generally treated as taxable income. Without a strategy, this can result in significant tax consequences, especially if a large balance is left until the final year.One of the biggest risks that individuals must be aware of when it comes to IRAs and estate planning is the “tax spike.” If a beneficiary delays withdrawals and then takes a lump sum in year ten, that distribution can push them into a much higher tax bracket. It may also affect other areas of their financial life, such as eligibility for certain deductions or credits. Instead of preserving wealth, the inheritance can shrink quickly due to avoidable tax exposure.
What can be done?
A more effective approach is to plan distributions across multiple years. By taking smaller, consistent withdrawals, beneficiaries can spread the tax burden and potentially stay within lower tax brackets. This strategy requires coordination with income levels, career changes, and other financial goals. In some cases, accelerating distributions in lower-income years or balancing them against other deductions can further reduce overall tax liability.Another important consideration is timing. In the years immediately following the rule change, there was some uncertainty about how required distributions would be enforced within the next ten years. The IRS provided temporary relief from certain penalties during that transition. However, 2026 marks the end of that leniency. Going forward, failing to follow the required timing rules can result in penalties, making careful planning even more important.At the end of the day, inherited IRAs are no longer passive assets that can be left untouched for decades. They require active oversight and a clear withdrawal strategy from the beginning. ]]>On Behalf of Cushing & Dolan, P.C.<![CDATA[Using joint trusts to maximize step-up in basis protections]]>https://www.cushingdolan.com/?p=551442026-05-07T00:11:38Z2026-05-07T00:11:38ZWhat is a step-up in basis?
A step-up in basis is the adjustment of the fair market value of critical assets at the time of an owner's death. In many joint trust scenarios, surviving spouses may only be eligible for a partial step-up of trust assets, resulting in substantial capital gains tax exposure.
The surviving spouse has substantial unrealized capital gains, which are essentially profits on paper for resources that may have appreciated in value, although they do not take any steps to access that value. Their liability may then pass to their beneficiaries after they die due to the increased fair market value of trust assets.
Certain types of trusts offer better protection
More thorough, advanced trust structures can help provide enhanced financial protection for surviving spouses and other joint trust beneficiaries. A Joint Exempt Step-Up Trust (JEST) offers protection for both spouses during their lives and for surviving spouses when one spouse passes.
Assets held in a JEST remain in the initial trust while both spouses are alive. Once one spouse passes, a portion of the resources transfer to a Credit Shelter Trust to maximize the exemption available to the deceased spouse, while other assets move into a Qualified Terminable Interest Property (QTIP) trust for the surviving spouse. Other options may include a Spousal Lifetime Access Trust (SLAT) or a Grantor Retained Annuity Trust (GRAT).
Creating a trust that allows for the adjustment of the fair market value of critical resources can protect surviving spouses and other beneficiaries from some substantial capital gains taxes when both of the initial trustors eventually die. Working with an estate planning firm familiar with more complex trusts can be crucial for the protection of married couples concerned about preserving their resources and limiting tax exposure.]]>On Behalf of Cushing & Dolan, P.C.<![CDATA[The differences between MassHealth and NH Medicaid]]>https://www.cushingdolan.com/?p=550952026-04-30T08:31:05Z2026-05-04T08:29:35ZMassHealth has unique state rules
MassHealth is an umbrella program that includes both the Children's Health Insurance Program (CHIP) and standard Medicaid. Children, families, people with disabling medical conditions and older adults all receive medical coverage through the same program.
As is true of Medicaid in every state, MassHealth is a state program partially regulated by federal rules. Massachusetts used federal waivers to expand MassHealth coverage. More vulnerable people may be eligible for MassHealth, especially later in life when dealing with intensive long-term care needs, than in states with standard Medicaid programs.
Those in New Hampshire can access Medicaid benefits through the standard waiver system when they require home or community-based services. They can also apply for benefits to pay for their nursing home costs.
Factors, including household income and the severity of medical challenges, directly influence eligibility for long-term care benefits through Medicaid or MassHealth. Applicants in Massachusetts may be able to qualify for community and in-home support with higher income levels than applicants in New Hampshire.
Those planning for future Medicaid eligibility need to work with an attorney familiar with state-specific rules. Clarity on income and asset restrictions, as well as the potential waivers available to applicants, can help older adults maximize their benefits and decrease the likelihood of coverage delays due to Medicaid lookback penalties. They can also potentially protect resources from estate recovery efforts after they die.
Changing asset ownership, making strategic gifts, completing a spend-down plan and funding a trust can all help those concerned about their future Medicaid or MassHealth eligibility. Consulting with an experienced elder law attorney familiar with New England Medicaid programs is of the utmost importance for those concerned about covering long-term care costs in their golden years. A lawyer's guidance can help people to better ensure that they are eligible when they need support the most.]]>On Behalf of Cushing & Dolan, P.C.<![CDATA[Using ethical wills to establish a positive legacy]]>https://www.cushingdolan.com/?p=550932026-04-30T08:22:52Z2026-04-30T08:22:52ZWhat is an ethical will?
An ethical will is a personal or philosophical document added as a supplement to legally binding paperwork in an estate plan. Ethical wills may outline an individual's personal moral beliefs to provide guidance during estate administration and to assist their loved ones with navigating challenging situations after their passing.
They may include information about a family's history. Some people use an ethical will as a brief autobiography to talk about their personal experiences and the legacy they want to leave after they die.
Ethical wills are also sometimes useful for those who want to express their love and devotion to family members in a concrete manner after their passing. Those who have been estranged from family members may use an ethical will as an opportunity to extend forgiveness. They can also express their gratitude to those who provided them with support throughout their life.
In an increasingly digital world, an ethical will can also serve as a means to discuss an electronic legacy, such as the conversion of a social media profile to a legacy account and how to address the decedent’s digital footprint after their passing.
Many people refer to ethical wills as the emotional heart of an estate plan that provides clarity and promotes family harmony. It can also help establish a consistent family narrative that may pass down through generations of the family. People may also refer to ethical wills as legacy letters or letters of intent.
Unlike wills and other estate planning documents that must be written instruments, ethical wills can be audio recordings or videos. Creating numerous separate documents for individual family members is also an option.
Testators thinking about their long-term legacy often need to expand beyond basic legal documents to achieve their most important goals. Working with an experienced estate planning attorney can help people craft ethical wills to supplement their legally-binding documents. The right collection of paperwork can provide guidance, promote family unity and establish a lasting, meaningful legacy.]]>On Behalf of Cushing & Dolan, P.C.<![CDATA[What you must know about the new reporting process for LLC chains]]>https://www.cushingdolan.com/?p=550682026-04-20T17:13:03Z2026-04-20T17:13:03ZManaging a chain of Limited Liability Companies (LLCs) once meant a simple annual filing. In 2026, it means dealing with a high-stakes set of rules that carry serious consequences for missed steps. One overlooked deadline can set off a chain reaction that puts your clients' assets at risk. To stay ahead, you need to understand three critical pillars: anniversary timing, new federal exemptions and the threat of administrative dissolution.
How one missed filing can break the chain
When one LLC in a complex chain falls out of compliance, the damage rarely stays contained. Think of it as a broken link. If the state dissolves a subsidiary for failing to meet its reporting obligations, the corporate veil protecting that section of the chain can disappear. In plain terms, that means the business loses its legal shield against outside threats. Outside parties may then pursue legal claims directly against parent entity assets. For advisors managing layered structures, this is not a theoretical risk. It is an immediate one. Therefore, knowing what is at stake is important. But knowing exactly which requirements apply makes all the difference.
Three new reporting rules every advisor must track
With so much at stake, knowing the specific rules that govern LLC chains in 2026 is your first line of defense. Three key requirements stand out as the most critical for advisors managing complex structures. Here is what you need to keep on your radar:
The anniversary rule: Massachusetts ties each LLC's Annual Report deadline to its original formation date, meaning every entity in your chain may carry a different due date and missing even one can cause serious problems for the entire structure.
The Federal Beneficial Ownership Information (BOI): Domestic U.S. LLCs and U.S. citizens now qualify for a broad exemption from filing BOI reports with the Financial Crimes Enforcement Network (FinCEN), but this federal relief does not eliminate your state-level filing obligations in Massachusetts.
The risk of administrative dissolution: If any LLC in your chain fails to file its annual report for two consecutive years, the Secretary of the Commonwealth can dissolve that entity, stripping away the legal protections it provides.
Each of these rules carries real consequences on its own. Together, they make a strong case for building a proactive compliance system across every entity in your chain.
Keep your business structure fully protected
Staying compliant across a complex LLC chain takes more than good intentions. It takes a clear understanding of the rules, consistent attention to deadlines and the right support in place before problems arise. The 2026 reporting landscape rewards those who plan ahead and penalizes those who wait. The more complex your business structure, the more important it becomes to have knowledgeable guidance on your side. The best time to review your compliance strategy is before a deadline passes, not after.]]>On Behalf of Cushing & Dolan, P.C.<![CDATA[Leveraging SLATs and GRATs in a high-interest environment]]>https://www.cushingdolan.com/?p=550152026-02-10T11:04:04Z2026-02-10T11:04:04ZNavigating estate planning amid rising interest rates requires careful planning. Tools like spousal lifetime access trusts (SLATs) and grantor retained annuity trusts (GRATs) can still help you transfer wealth to heirs while reducing taxes.
However, higher IRS rates create bigger challenges, affecting how much growth can pass tax-free. Understanding how these strategies work in a high-interest environment can help you make informed choices for your family’s financial future.
Adjusting SLATs amid higher rates
Higher rates can slow the growth of assets inside a SLAT, as investments may earn less relative to the IRS discount rate. SLATs let you move assets out of your taxable estate while giving your spouse indirect access if needed, preserving family wealth over time. The core benefit — keeping future growth tax-free for heirs — remains strong, even if rate changes temper inside growth.Adjusting SLATs naturally leads to considering GRATs. While SLATs focus on keeping wealth in the family over the long term, GRATs offer a way to pass high-growth assets to heirs more aggressively. Combining both tools can give you flexibility in how you manage transfers and taxes.
Making GRATs work despite the hurdle
Rising interest rates push up the IRS “hurdle rate,” making it harder for GRATs to pass significant value tax-free. With January 2026’s 7520 rate around 4.6%, the hurdle feels steeper. In a GRAT, you transfer assets but receive fixed annuity payments for a set term, essentially renting the assets to yourself. Strategies to improve outcomes include:
Funding GRATs with fast-growing assets, like stocks, that may outperform the IRS hurdle rate
Setting up GRATs over multiple years to spread risk and adjust for rate changes
Choosing shorter terms, typically 2-5 years, to limit exposure to market swings
These strategies often pair well with SLATs, giving you options to balance growth, access and family flexibility. Legal guidance can help determine which combination fits your goals and ensures compliance with IRS rules.
Planning with precision
Higher interest rates shift the rules of wealth transfer, making timing, asset selection and trust structure more critical than ever. Small adjustments in how and when you fund trusts can have a meaningful impact on what ultimately passes to heirs. Careful monitoring of rate changes and market performance helps align estate strategies with long-term goals while managing potential tax consequences.]]>On Behalf of Cushing & Dolan, P.C.<![CDATA[Which type of business entity is right for you?]]>https://www.cushingdolan.com/?p=549702025-12-17T12:48:01Z2025-12-17T12:34:26ZSole proprietorship
Recognized as the most common form of business entity for small businesses, sole proprietorship involves a single owner. Under this business model, the owner is fully responsible for their daily operations. They also manage their profits, debts and taxes on their own or with the help of an accountant.
Since they can operate under their own name, they do not need to register as a sole proprietor with their state. Four common examples of sole proprietorship businesses are photography studios, bakeries, grocery stores and catering services.
Partnership
A business partnership is a formal arrangement between two or more people. When someone builds a business with another party, they agree to operate the business as partners and share the profits equally.
The state of Massachusetts follows the Uniform Partnership Act. This act exists as a general guidance for partnership agreements, defining their duties with conciseness and how the business’ liabilities must be managed amongst the partners.
Limited liability company (LLC)
Also known as a hybrid entity, LLC carries the characteristics of both a corporation and a partnership. This business model is not subject to taxes; rather, the business’ profits pass through the owners, who must then pay the taxes on their personal returns.
When entrepreneurs choose this type of structure for their business, they are able to carry a liability protection similar to a corporation, while having the freedom to choose how their business will be taxed.
Your business’ future is in your hands
By taking your time to understand the diverse types of business formations, you can make informed decisions that can guide your business in the right direction.]]>On Behalf of Cushing & Dolan, P.C.<![CDATA[3 important considerations when selling a business]]>https://www.cushingdolan.com/?p=549992025-12-29T21:59:25Z2025-12-08T11:21:37ZThe sale of a business may have been the goal of the entrepreneur who started the company. Other times, changing personal circumstances may make the sale of a business necessary. Medical challenges, divorce and changing professional aspirations can all lead to a business owner selling their company.
Ideally, a business sale generates enough revenue to compensate the owner for the investments that they have made and to set them up for their next venture. Following the right procedures before selling a business is critical for the optimization of the final sale price and the success of the transaction. What matters do business owners often need to address when selling a company?
1. Determining a reasonable asking price
The amount sought when selling a business depends on many different details. There are numerous ways to establish a realistic fair market value for a company. Future revenue, physical resources and contracts can all factor into the business valuation process. Choosing the right valuation method and gathering accurate information about the company are of the utmost importance.
2. Making appropriate disclosures
Business owners listing their companies for sale typically need to provide information about the company’s historic performance and future prospects to potential buyers. Gathering critical documentation and ensuring its accuracy before listing the company is of the utmost importance. Missing paperwork or inaccurate documents can lead to a buyer backing out of a transaction at the last minute. Sellers generally need to collect, review and organize information that they must provide to the buyer in advance to ensure that they can provide an accurate and transparent assessment of the organization.
3. Connecting with the right buyers
There are many ways to market a business for sale, and each has its own unique benefits and drawbacks. Factors including the cost, the intended audience and even the impact on existing clients, customers or employees can factor into how an owner markets their company. In some cases, they may put up a public sign indicating that the business is for sale. Other times, they may begin the marketing process by reaching out to specific investors or competitors who have previously expressed interest in the organization. Many different complications can arise during a business sale, and leaders may need assistance managing the sale process while continuing to run the company. Working with an attorney familiar with large business transactions can make selling a business less challenging and less risky.]]>On Behalf of Cushing & Dolan, P.C.<![CDATA[When do estate beneficiaries owe capital gains taxes?]]>https://www.cushingdolan.com/?p=549982025-12-29T21:57:26Z2025-11-17T11:18:45ZThere are multiple types of taxes that can affect the value of an estate and the inheritance that beneficiaries or heirs receive. Especially large estates could be subject to estate taxes if the decedent didn't plan in advance to minimize that liability.
The deceased individual and the estate could potentially owe income taxes. The beneficiaries or heirs who inherit properties from the estate may also have a responsibility to pay capital gains taxes. Capital gains taxes are a federal tax imposed on the revenue generated after the sale of an asset that has appreciated in value. Capital gains taxes may apply when people sell businesses, real property, high-value collectibles or investment holdings. When do the beneficiaries or heirs receiving property from an estate need to address capital gains taxes?
There are some exemptions available
Depending on the circumstance, beneficiaries may not actually owe capital gains taxes. For example, perhaps the primary beneficiary of an estate is the surviving spouse of the decedent. They may no longer be able to afford or maintain the home where they lived while they were married and may choose to sell the home. In such cases, they are eligible for an exemption of up to $250,000 in appreciated equity before they owe capital gains taxes. The relationship between the beneficiary and the nature of the assets liquidated, as well as the overall value of those resources, how long the new owner holds them and how much they have appreciated in value since their acquisition, can influence the tax rate that applies and the total amount of capital gains taxes due. Capital gains tax rates can range from as low as 0% for long-term investments in some cases to as high as 37% when selling an asset held for a year or less. Those concerned about capital gains taxes may need support while they plan their estates or assist with estate administration. Personal representatives, beneficiaries, heirs and even testators creating their estate plans may need guidance to minimize capital gains taxes while simultaneously fulfilling federal tax obligations. Revealing the resources intended as an inheritance and the plan to sell them with an attorney familiar with estate administration and taxes can be helpful for anyone with an interest in an estate.
]]>On Behalf of Cushing & Dolan, P.C.<![CDATA[What is the 2026 estate tax threshold?]]>https://www.cushingdolan.com/?p=549972025-12-29T21:56:07Z2025-11-04T11:15:54ZSome people say that there are only two certainties in life. Death and taxes are the two absolutes that affect almost every human living in the United States. Everyone dies, and the vast majority of people pay taxes before they do.
In some cases, people may technically continue to owe taxes even after they die. The property that belongs to a deceased individual becomes their estate unless they have made prior arrangements. Those resources can then sometimes be subject to estate taxes. The federal estate tax is notorious for consuming a substantial amount of large estates if people do not plan carefully. The maximum tax rate at the federal level is a staggering 40%, and Massachusetts state estate taxes can consume up to another 16% of the estate’s value. Thankfully, the law permits an exemption, allowing many estates to completely bypass estate taxes. The exemption threshold shifts annually. How much property can people exempt before they owe estate taxes?
The 2026 limit is the highest ever
Annual adjustments to the federal estate tax exemption may make regular estate planning reviews necessary. As people's resources appreciate in value and the amount that they can exempt changes, they may need to adjust their plans accordingly. For those who died in 2025, the maximum exempt value of an estate was $13.99 million. The same progressive tax rate applies in 2026, but the exception limit is significantly higher. An individual who passes in 2026 can exempt up to $15 million in estate assets before federal estate taxes are a concern. The state exemption is lower, at just $2 million. Individuals with large investment portfolios, businesses and multiple real property holdings could be at risk of estate taxes. They may need to make strategic plans in advance. Recording new deeds, submitting transfer on death designations to financial institutions, making strategic gifts, donating resources to charitable causes and transferring resources to trusts are all ways that people reduce their estate tax obligations. Discussing personal priorities and holdings with an attorney familiar with estate tax regulations can help people optimize their estate plans. The right strategies can help testators minimize the tax rate that applies or completely avoid estate tax obligations.]]>