Long-Term Rentals
The financial operating manual for long-term rental owners.
A year holds few transactions and a handful of choices that set the next decade — the loan, the structure, the hold. Most get made by default, and a default costs years later.
Connected disciplines, each one a body of work rather than a list of posts.
Every discipline opens with the guide that makes the rest legible, then the concepts in the order they depend on each other, and the decisions they lead to.
Deal Analysis
What the property will actually collect, and what that makes it worth.
Financing
Debt as a tool, and knowing which direction it points.
Entity Structure
How far to separate the asset, the business, and yourself.
Bookkeeping & Reporting
Books you can stand behind at tax time, at renewal, and at sale.
Tax Strategy
Why your rental losses wait, and what releases them.
Wealth & Exit
What your equity is earning, and what it costs to move it.
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 Rental Pencil?
Pay Cash or Finance?
Should I Put My Rental in an LLC?
DIY, Bookkeeper, and Software
Can I Actually Use My Rental Losses?
Sell, 1031, or Refinance?
Other librariesShort-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.