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Massachusetts · Investor, mixed-use & residential
I work with property owners who think in NOI and cap rates: portfolio holders, mixed-use owners and investors scaling past their first few buildings. The transaction is the last step. Underwriting, ownership structure and tax timing come first.
Who I work with
Most of my clients already own property. They need someone who can read a rent roll and a T-12, see the deed and the entity behind it, and tell them what the next move does to their position.
Portfolio holders
Owners deciding what to sell, refinance, trade or hold, and in what order.
Mixed-use & small commercial
Retail-over-residential and small commercial, where leases and zoning drive value and financing.
Scaling investors
Investors with a few doors and the intent to grow, who want to set up structure before it gets expensive to fix.
I also represent residential buyers and sellers, and help families and fiduciaries sell inherited and estate property.
Approach
Every engagement follows the same sequence. Skipping a step is how owners end up selling the right building in the wrong entity, or in the wrong tax year.
01
Rent rolls, trailing-12 operating statements, debt terms, deeds and the entity map, reviewed together.
Output: a one-page position summary
02
How title is held, how the sale or purchase is financed, and how the tax consequences land. Coordinated with your CPA and attorney.
Output: a structure and timing plan
03
Pricing from NOI, not from comps alone. Marketing to the right buyer pool, or sourcing the right acquisition, and managing diligence to close.
Output: a closed deal on plan
04
Post-close setup: management, vendor systems and physical access control, so the asset performs the way it was underwritten.
Output: a building that runs
Services
Buy-side and sell-side representation for multifamily, mixed-use and small commercial property, priced and negotiated on income.
A structured look at every asset you own: performance against market, debt maturity, equity position and which property to move next.
Pro formas, cap rate and cash-on-cash analysis, value-add scenarios and stress tests on rent, vacancy and rate.
Sale timing around 1031 deadlines, replacement property sourcing, and coordination with your intermediary and tax advisor.
Lot, zoning, septic and conversion analysis for land, church and institutional buildings, and underused parcels.
Single-family and 2–4 family sales, including inherited property where executors need a clear process and a steady hand.
Field notes
Short technical notes on the issues that move value for income property owners. General information, not tax or legal advice. Your CPA and attorney should confirm anything that applies to you.
Valuation
Cap rate is NOI divided by price. It says what the market pays for a dollar of income today. It says nothing about leverage, appreciation or what you will actually earn. Those live in cash-on-cash and IRR.
Small moves in cap rate are large moves in value:
Operations
At a 6.25% cap rate, each $1 of annual NOI is worth $16 of value (1 ÷ 0.0625). Cutting $5,000 of recurring expense adds about $80,000 to what the building is worth.
That is why I start sell-side work with an expense audit: tax abatement eligibility, insurance re-bids, utility billing (RUBS or submetering where allowed), and service contracts nobody has re-bid in years.
Tax timing
In a §1031 exchange you have 45 days from the sale to identify replacement property in writing, and 180 days (or your tax return due date, if earlier) to close on it. A qualified intermediary must hold the proceeds.
The planning happens before the listing: a realistic replacement pool, lender pre-approval, and a sale date chosen around the calendar.
Tax exposure
Residential rental buildings depreciate over 27.5 years, nonresidential over 39. On sale, the depreciation you took is generally taxed as unrecaptured §1250 gain at up to 25%, separate from capital gains.
A long-held building with a low basis may net far less than its price suggests. That changes whether you sell, exchange, refinance or hold.
Structure
Before adding a property, look at how everything is already held:
Massachusetts diligence
Calculators
Two working calculators, each loaded with an example you can overwrite with your own figures.
Build NOI from rents and expenses, see the value at a market cap rate, the cap rate implied by an asking price, and what each dollar of NOI is worth.
Open the calculator → DispositionFederal capital gains, depreciation recapture, the 3.8% net investment income tax, Massachusetts tax and the 4% surtax, and what a 1031 exchange would defer.
Open the calculator →Start a conversation
A first conversation is a working session, not a pitch. Share as much or as little as you like.
Call or text 508-809-0178
investors@zackwhiting.com