Short-Term Rentals
The financial library for short-term rental owners.
Revenue is earned operationally rather than collected, the cost stack is longer than most owners expect, and the tax treatment turns on how the property is used rather than on what it is.
Connected disciplines, each a set of guides that build on each other.
Every discipline opens with one guide to read first, then the guides that build on it, and the decisions they lead to.
Deal Analysis
Know whether a property makes money before you buy it.
Financing
Fund the property without letting the loan run the deal.
Entity Structure
Hold the property so one lawsuit, tax, or deal can't risk everything.
Bookkeeping & Reporting
Keep clean books that show what's really happening — and stand up for taxes and lenders.
Tax Strategy
Understand what you legitimately owe and legitimately save.
Wealth & Exit
Keep it, grow it, and plan the exit before you sell.
Start with the decision in front of you.
Most readers arrive with one question. Each of these is a full guide, and each sits in a discipline you can then work through from the start.
Does This Deal Actually Pencil?
Should I Pay Cash or Finance My STR?
Should I Put My STR in an LLC?
Should Each Property Have Its Own Books?
The STR "Tax Loophole": Do I Qualify to Offset My W-2 Income?
Should I Sell, 1031, or Refinance My STR?
Other business typesLong-Term Rentals
A letter for people who run property as a business. One idea at a time on the financial side of ownership — what changed, what it means, and what an operator should do about it. Written for short-term and long-term rental owners alike.