Short-Term Rentals
The financial operating manual 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 one a body of work rather than a list of posts.
Every discipline opens with a plain-language manual, then the guides that build it, and the real 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 get out without handing a third to the IRS.
Start with the decision in front of you.
Most readers arrive with one question rather than a curriculum. Each of these is a full guide, inside a discipline you can then work through properly.
Does This Deal Actually Pencil?
Should I Pay Cash or Finance My STR?
Should I Put My STR in an LLC?
DIY, Bookkeeper, and Software
The STR "Tax Loophole": Do I Qualify to Offset My W-2 Income?
Should I Sell, 1031, or Refinance My STR?
Other librariesLong-Term Rentals
The weekly letter for people who run property as a business. One idea a week 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.