Long-Term Rentals
The financial library 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 a set of guides that build on each other.
Every discipline opens with one guide to read first, 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. Each of these is a full guide, and each sits in a discipline you can then work through from the start.
Does This Rental Pencil?
Pay Cash or Finance?
Should I Put My Rental in an LLC?
Should Each Property Have Its Own Books?
Can I Actually Use My Rental Losses?
Sell, 1031, or Refinance?
Other business typesShort-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.