.), Designing and Furnishing (amenities, design, theme, linens, etc), and operating (Insurance, Property management or self-management, Tech & Tools, Cleaners & handy people, etc)All of these could be covered depending on who you work with that can cover each topic. 

You'll need to compare apples to apples. 40k seems like a low number to design, furnish and amenitize a competitive short term rental projected to do $100k. 

As others have mentioned you start on Form 4562, but in my opinion you should have a simple google sheet or excel to track all of this for your properties.

A simple example is that they called to tell me the hose was left on in the pool.  

ROBS designed to invest retirement funds into an active business.

(Also, ask them who they use to design it.)

If booking direct and he has no reviews I would have him sign a simple lease, do a BG check, and have a reasonable deposit.

(to keep things simple)Property was primary residence for Person A from original purchase until 01/2020.

Turning a single-family into a multi-family is simple.

Simple...