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Ongoing engagement · Real estate investors · Greater Boston

Most CPAs file your return. Almost none plan your year.

By the time anyone opens your return, every decision that mattered has already been made. The entity, the basis, the hours, the disposition, the timing of the sale. Real estate tax is won during the year and merely recorded in April. This is the engagement for owners who want the planning, not just the filing.

The problem with April

Every one of these is decided before your return exists.

A filing-only relationship can report what happened. It cannot change what happened. These are the moments where the money is actually made or lost, and all of them close before the year does.

Before you buy
Whether the property can support the strategy at allBuilding-to-land ratio, the component mix, and whether the operating plan clears the test you are trying to meet. A property chosen without this in mind is harder to fix afterward.
By mid-year
Whether your hours will actually clear material participationThe count only helps while there is still year left to change it. A shortfall discovered in April is a shortfall you live with.
During the work
Whether a component you replaced gets written off or buriedThe partial asset disposition election has to be made on a timely filed return. Miss the year and the old roof stays on your depreciation schedule alongside the new one.
Before you list
Whether a sale becomes an exchange or a tax billOnce the property is under agreement the options narrow fast, and the 45 and 180 day clocks start at closing whether or not anyone has planned for them.
Any time
Whether an entity change helps or just adds a filingEntities get recommended constantly and earn their keep rarely. The honest answer is often that the one you have is fine.
What the engagement is

Three parts, and the third is the one people skip.

01

Planning through the year

Scheduled check-ins while decisions are still open, plus availability when something unplanned comes up. A purchase, a sale, a major capital item, or a change in how much time you can give the portfolio. Those are the calls that need to happen in the moment, not at year end.

02

The return, prepared by the person who planned it

Federal and Massachusetts returns, the entity returns, the depreciation schedules, the basis tracking. Prepared by the person who chose the positions rather than handed to someone reconstructing them from receipts.

03

The file that supports the position

Aggressive positions are not won by being right. They are won by being documented. Studies, elections, participation records, and workpapers assembled as the year goes, so the support exists before anyone asks for it.

Why this practice and not another

The person who plans it is the person who signs it.

Most real estate tax planning is sold by people who never see the return, never see the property, and are never on the hook for either. Here it is one person holding three licenses, which is why the advice tends to be more conservative rather than less. It is his signature on the return.

CPA

Signs the returns and takes the positions.

Licensed MA real-estate agent

Affiliated with Profitable Properties Boston LLC. Sees the property, not just the closing statement. The buy-side offer →

MA Construction Supervisor

Knows what a renovation actually costs and what it actually replaced.

Fit

Worth being honest about who this suits.

An ongoing engagement is more than most people with a rental need. If a straightforward return is genuinely all you require, a planning relationship is not worth what it costs you.

This fits if

  • You own rental property and expect to buy, sell, or substantially renovate in the next year or two.
  • You are running a strategy that has to be maintained — REPS hours, an STR that has to hold its average stay, a cost segregation already taken.
  • You have real W-2 or business income alongside the real estate, which is where the planning and the mistakes both concentrate.
  • You just did something significant and want the position defended properly rather than filed and hoped over.

This does not fit if

  • You own one stable rental with nothing changing. A competent preparer is the right answer and costs less.
  • You want a specific outcome confirmed rather than assessed. If the answer is that it does not work, that is the answer you will get.
  • You want the aggressive version regardless of support. Positions here get taken when the documentation can carry them.
  • Your real estate sits outside Massachusetts and New Hampshire. Ask, but the answer may be a referral.
Ground rules

What you can hold us to.

The honest no.If a strategy does not work for your facts, you hear that plainly and early, in writing. A documented no is worth more than an expensive maybe.
No guaranteed outcomes.Nobody can promise a tax result, and the ones who do are selling something. What gets committed to is the analysis, the documentation, and the deadlines.
Scope in writing.What is included, what is not, and what it costs are agreed before work starts. Quoted after a fit call, because the return drives the number.
Affiliations disclosed.The same client can end up paying an affiliated brokerage, contractor, or management company. Where that is true you are told in writing, before you decide anything.
A fit call, 20 minutes

Bring the portfolio and the year ahead.

What you own, what you are planning, and what your current return looks like. You will get a straight read on whether an ongoing engagement is worth it for you, including when it is not.

Book a fit call → Email Matt directly
matt@wrtadvisors.com · (617) 648-7413
Sent here by your CPA, attorney, or qualified intermediary? Say so on the call. Referred clients stay their professional's client, and the referring professional is copied on what we produce. The arrangement we offer other professionals is set out on the partner page.