Tax and Estate Planning

Tax and estate planning for complex financial decisions

Tax and estate planning connect decisions about your investments, income, family, business interests, and legacy. Great Point Wealth Advisors helps individuals and families evaluate those decisions, model trade-offs, and coordinate implementation with their CPA and estate attorney.

We advise on strategy and coordination. We do not prepare tax returns or draft legal documents. Instead, we help your specialists work from one plan while keeping your broader financial goals in view. This work may be especially relevant when you are navigating a liquidity event, concentrated position, business transition, inheritance, charitable goals, or Massachusetts estate-tax exposure.

How we work with your CPA and attorney

The distinction matters, so we lead with it:

• We advise on tax strategy. We do not file returns, sign as preparer, or provide formal tax opinions. We work alongside your CPA — or introduce you to one from our network — to make sure the return reflects the strategy.
• We advise on estate strategy. We do not draft wills, trusts, powers of attorney, or health care directives. We work alongside your estate attorney — or introduce you to one from our network — to make sure the documents implement the strategy.
• We own the coordination. Modeling, scenario analysis, funding decisions, beneficiary designations, gift tracking, and follow-through are ours. You should not have to be the project manager on your own plan.

Is this planning relevant to you?

Tax and estate planning may be worth exploring if you:

• want your CPA, attorney, and wealth advisor working from a coordinated strategy;
• are approaching a business sale, inheritance, relocation, retirement, or other liquidity event;
• have concentrated stock, business interests, charitable goals, or multigenerational transfer decisions; or
• want to review beneficiary designations, estate documents, or potential Massachusetts estate-tax exposure.

Your circumstances determine which strategies are appropriate. We begin with your goals, current documents, investments, and family context before recommending a path.

Tax planning: mitigating what you owe today and in the future

We approach taxes on a multi-year basis. A one-year filing view often produces the wrong answer — accelerating income into a low-bracket year, deferring a Roth conversion to a bad one, or missing a harvesting window because no one was looking. Our planning is built around a rolling multi-year projection that we revisit every year and update for any material change.

Areas we advise on

Income tax planning

• Multi-year federal and state tax projections
• Marginal vs. effective rate analysis and "fill-the-bracket" strategies
• AMT and Net Investment Income Tax exposure
• State residency planning, including domicile changes out of Massachusetts where appropriate
• Estimated tax coordination with your CPA

Investment-related tax planning

• Asset location across taxable, tax-deferred, and Roth accounts
• Tax-loss harvesting and, in selected years, capital-gain harvesting
• Wash-sale management across household accounts
• Municipal bond positioning where the after-tax yield beats the taxable alternative
• ETF vehicle preference for lower embedded capital gain distributions
• Cost-basis method selection and specific-lot identification

Retirement account tax planning

• Roth conversion ladders in low-income years, including the runway between retirement and Required Minimum Distributions under IRS rules
• Backdoor and "mega backdoor" Roth strategies where the plan allows
• Net Unrealized Appreciation (NUA) analysis on employer stock in a 401(k)
• SECURE 2.0 planning, including the shift in RMD age and 529-to-Roth rollovers
• Inherited IRA distribution planning under the 10-year rule

Executive compensation & concentrated stock

• ISO/NSO/RSU/ESPP timing and tax modeling
• 83(b) elections for restricted stock
• Qualified Small Business Stock (Section 1202) planning for founders
• 10b5-1 trading plans and diversification pathways for concentrated positions

Business owner tax planning

• Entity structure review with your CPA (S-corp, partnership, C-corp)
• Reasonable compensation and distribution strategy
• Retirement plan design (Solo 401(k), SEP, SIMPLE, cash balance)
• Qualified Opportunity Zone reinvestment on sale proceeds
• Sale structure — asset vs. stock, installment, earnout, F-reorganization — modeled for after-tax proceeds

Charitable tax planning

• Donor-Advised Fund contributions of appreciated securities
• "Bunching" multiple years of charitable giving into one to clear the standard deduction
• Qualified Charitable Distributions from IRAs after age 70½
• Charitable Remainder Trusts and Charitable Lead Trusts, coordinated with the estate plan

Estate planning: transferring wealth efficiently and intentionally

Estate planning is where the largest single tax savings in a wealthy family's plan often live. It is also where procrastination is most expensive: strategies that work brilliantly today become unavailable at death, and some become dramatically less powerful if interest rates or exemptions change first.

We start every estate planning engagement with two questions:

1. What do you actually want to happen — for your spouse, your children, your grandchildren, and the causes you care about?
2. What is the tax cost of the current documents accomplishing that outcome, and can we reduce it materially without compromising what you want?

Then we build the plan.

The Massachusetts context

Massachusetts imposes an estate tax on estates above $2 million, a threshold that is not indexed for inflation. The federal exemption, by contrast, was raised to $15 million per individual ($30 million per married couple) beginning in 2026 under the One Big Beautiful Bill Act, and is now permanent and indexed to inflation starting in 2027. That gap catches many Boston-area families by surprise, because a primary residence, a second home on the Cape or in the mountains, retirement accounts, and life insurance can push a household well past $2 million long before anyone considered themselves "estate-tax exposed." Planning around this state-level threshold is a core part of what we do.

Foundational estate documents

Before any advanced strategy, every client should have — and have current:

• Last will and testament
• Revocable living trust, where appropriate
• Durable power of attorney
• Health care proxy and HIPAA authorization
• Guardianship designations for minor children
• Correct beneficiary designations on every retirement account, life insurance policy, annuity, and transfer-on-death account
• Correct titling of real estate, business interests, and financial accounts

We audit all of the above at onboarding, flag gaps and inconsistencies, and coordinate with your attorney to bring the documents current. Beneficiary designations in particular override the will, and errors here are one of the most common — and most expensive — mistakes we see.

Lifetime gifting strategies

Moving assets out of the estate during your lifetime is often the single most effective tax lever available. We help clients design and execute:

Annual exclusion gifting. The annual gift tax exclusion allows each individual to give up to $19,000 per recipient in 2026 with no gift tax return required and no use of the lifetime exemption. Married couples who elect gift-splitting can move $38,000 per recipient per year. A couple with three children and six grandchildren can move $342,000 out of the estate annually using this exclusion alone — more than $3.4 million over a decade, plus all future appreciation on those transferred assets. Gifts to a non-U.S.-citizen spouse have a separate 2026 annual exclusion of $194,000.

Direct payment of tuition and medical expenses. Payments made directly to an educational or medical institution on someone else's behalf are unlimited and do not count against the annual exclusion or lifetime exemption. For clients funding grandchildren's private school or college, this is powerful and underused.

Use of the lifetime gift and GST exemption. Larger lifetime gifts, funded with the lifetime exemption — $15 million per individual ($30 million per married couple) in 2026, made permanent and indexed to inflation beginning in 2027 under the One Big Beautiful Bill Act — move both the gift and all future appreciation out of the estate. Coupled with generation-skipping transfer (GST) exemption allocation at the same $15 million level per individual, these gifts can benefit multiple generations without additional transfer tax at each level.

529 plan superfunding. 529 contributions can be front-loaded with five years of annual exclusion gifts in a single year per beneficiary, accelerating tax-free education funding while still using only annual exclusion rather than lifetime exemption.

Spousal gifts and portability elections. Coordinating gifts between spouses and preserving portability of the deceased spouse's unused exemption (DSUE) so no exemption is wasted at the first death.

Grantor Retained Annuity Trusts (GRATs)

GRATs deserve their own section because they are one of the most powerful — and most under-used — wealth transfer tools for clients with concentrated positions or expected appreciation.

The mechanics. You transfer an asset into a GRAT and, in exchange, retain the right to receive fixed annual annuity payments back for a set term. The IRS values your retained annuity using the Section 7520 rate in effect at the time of funding. If the trust assets grow faster than that rate, everything above the rate passes to your beneficiaries free of gift and estate tax at the end of the term. If they don't, the assets simply return to you — the "downside" is essentially the legal cost of setting the GRAT up.

Where GRATs shine.

• Pre-IPO equity, concentrated public stock, or founder shares expected to appreciate
• Rebalancing a concentrated stock position while transferring the expected appreciation to heirs
• Environments where the 7520 rate is comparatively low
• Clients who have already used or are unwilling to use lifetime exemption

How we run the analysis.

• Model the projected annuity payments and remainder based on expected asset volatility and return
• Evaluate short-term "rolling" GRATs vs. longer-term GRATs, and the trade-offs of each
• Coordinate with your attorney on trust drafting, funding mechanics, and the annual valuation of in-kind annuity payments
• Track annuity payments and remaining term so nothing slips through operationally

For a plain-language primer on the mechanics, see Fidelity's What is a grantor retained annuity trust (GRAT)?.

Other advanced strategies we advise on

For families with meaningful net worth, GRATs are often one tool among several. We evaluate and, when appropriate, coordinate the implementation of:

Spousal Lifetime Access Trusts (SLATs). Irrevocable trusts funded for the benefit of a spouse (and often descendants) that remove assets and future appreciation from the estate while preserving indirect access through the spouse-beneficiary.

Irrevocable Life Insurance Trusts (ILITs). Life insurance held inside an ILIT is excluded from the taxable estate, converting a taxable death benefit into a tax-efficient wealth transfer. We coordinate premium gifting, Crummey notices, and policy review.

Intentionally Defective Grantor Trusts (IDGTs) and installment sales. Selling appreciating assets to an IDGT in exchange for a promissory note freezes the estate value at today's price, transfers all future appreciation to the next generation, and — because the trust is "defective" for income tax purposes — allows the grantor to keep paying the trust's income tax as an additional tax-free gift.

Family Limited Partnerships and LLCs. Consolidating family assets in an entity, then gifting or selling non-voting interests at valuation discounts for lack of control and marketability. Useful for real estate portfolios, operating businesses, and concentrated investment holdings.

Charitable Remainder Trusts (CRTs) and Charitable Lead Trusts (CLTs). Structures that split benefits between family and charity, generating current income tax deductions and reducing the taxable estate while satisfying philanthropic intent.

Qualified Personal Residence Trusts (QPRTs). Transferring a primary or vacation home to heirs at a discounted gift-tax value while retaining the right to live there for a term of years.

Dynasty trusts and GST planning. Long-duration trusts, typically sited in favorable jurisdictions such as Delaware, South Dakota, or Nevada, that leverage GST exemption to benefit multiple generations without additional transfer tax at each generational level.

Business succession planning. Buy-sell agreements, key-person insurance funding, valuation planning, and coordination of an exit or intergenerational transfer.

Charitable planning through Donor-Advised Funds and private foundations. For clients with meaningful annual giving, we help decide between a DAF, a private foundation, or a combination, and integrate the giving vehicle with the estate plan.

What working with us looks like

For most clients, the tax and estate planning workstream follows a predictable cadence:

• Onboarding. Document collection, beneficiary audit, current-state modeling of federal and Massachusetts estate tax exposure, and identification of the two to three highest-impact opportunities
• Strategy design. Written recommendations with modeled outcomes, tax savings quantified in dollars, and a proposed sequence of implementation
• Implementation. Direct coordination with your CPA and attorney, including drafting instructions, funding schedules, and follow-through checklists
• Annual review. Updated tax projection, updated estate exposure, gift-tracking summary, and any adjustments for new law or new circumstances
• Ad-hoc. Any liquidity event, business sale, inheritance, relocation, or major law change triggers an out-of-cycle review

Our role, at every step, is to make sure the plan is not sitting in a binder. It should be running, measurably, in the background of your life. The work is organized around a shared implementation roadmap so you, your CPA, your attorney, and Great Point can see the decisions, responsibilities, and timing.

Starting the conversation

Ready to discuss your situation? Contact Great Point Wealth Advisors to submit an inquiry about your goals, current planning, and the decisions ahead. If you are still exploring how tax and estate planning fit into broader wealth management, see our Retirement and Financial Planning page.

Great Point Wealth Advisors is an independent, fee-only Registered Investment Advisor. We do not prepare tax returns or provide legal advice, and nothing on this page constitutes tax or legal advice for any specific person. Tax and estate strategies described are examples of what we advise on and are implemented in coordination with your CPA and attorney. Tax laws change frequently; current federal and state thresholds should be confirmed at the time of any planning decision.