March is when you discover the number. October is when you set it. Matt finds the house, does the math, and signs the tax form — start to finish.

At Massachusetts' top brackets, you keep about 58¢ of every new dollar you earn.* On the money we legally protect, you keep the whole dollar. Going from 58¢ to $1 is like a 72% raise on that money — and nothing about your job has to change. Just your paperwork, and your calendar.
*Illustrative: top federal bracket plus Massachusetts income tax and the 4% surtax on income over ~$1.1M. Your rates depend on your facts. Estimates are educational, not tax advice — the point of the Blueprint is to replace estimates with your actual number, in writing.
It's written into the tax law on purpose, and wealthy families use it every year. Three parts have to work together — and someone has to be willing to sign the tax form at the end.
When guests stay about a week or less and you help run the place yourself, the tax rules treat it like a business you work in. Done right, its paper losses can cut the tax on your paycheck.
An engineer values every piece of the property. The tax code then lets you deduct a big chunk of the price — often 25–30% of it — this year, instead of spreading it over decades.*
The part everyone skips — and the first thing the IRS reads. Which hours, which dates, who did what. We build your records the way the IRS likes to read them.
No. It has to be a short-term rental — but it doesn't have to be a place you never see. Plenty of clients pick a property their own family actually uses.
A straightforward rental you never stay in. Simplest path — no personal-use days to track, no calendar to protect.
A lake house or cabin you'd actually vacation in — and rent out the rest of the year. The tax code caps your own personal days to keep the write-off; we build that calendar with you so you never cross the line.*
Two sliders. No email needed. This shows the ballpark — the Blueprint gets your exact number, in writing.
*A ballpark for education, not tax advice. It assumes the engineer's study finds a first-year deduction of ~25–30% of the price, that the losses fully count against your income under the short-term-rental rules, and rough 2026 federal + MA rates. Whether you qualify depends on facts a slider can't see — that's what the Blueprint checks. "Could," never "will."
The rule isn't the hard part. The hard part is how many people you have to trust to pull it off. Five, normally — or one office that runs it start to finish.
Every step exists because skipping it is how people get in trouble. It's called a shield because it's built to be defended.
Your return, read. Your number, in writing — or an honest "this isn't for you."
We walk from deals that don't make sense. A tax break never fixes a bad house.
Bought, furnished, and taking guests this year. One office runs the calendar.
The engineer's study that unlocks the big first-year number.
A simple diary system. About two hours a week — we set it up for you.
If the IRS ever writes about it, Matt answers the letter. Free.
Bring your last tax return. You leave with a number, in writing: what this could take off this year's bill, whether you truly qualify, and what has to happen by when. No house, no study, no filing — unless the numbers say so.
Go ahead with the plan, and the $1,997 comes off your bill — so the Blueprint costs nothing if you act on it. The house hunt, the setup, and the year-round plan get priced after we see what it finds.
Book the Blueprint call →It's written into the law on purpose and used by wealthy families every year. We just do the paperwork the way the IRS wants to see it — that's the whole job.
About 100 hours a year — roughly two hours a week — and you get the checklist and the log system. That's the honest price of the discount. If you won't do the hours, we'll tell you not to buy.
Then the person who answers the letter is the person who signed your return: Matt. At no extra charge.
"I'd rather lose a commission than sign a return I don't believe in. If the math doesn't clear, I'll tell you not to buy — that's the difference between a strategy and a sales pitch."
— Matthew Wessels, CPA, MBABook the call. Bring your last tax return. If we can't find savings worth 3× the fee, you don't pay — and if this isn't for you, you'll hear that too.