I’m always thinking about how something will photograph so my other advice is to make sure the photos are top quality because that’s all someone has to go off when booking. 

I'm not a fan of just including a flat fee in rent.

Quote from @Lawrence Mitchell: I've read a few books on real estate and something the majority of them had in common was the BP community so I would like to see what it has to offerHey @Lawrence Mitchell, welcome to the BP Forum!

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.2.

The trade off course for STR route is more management/cleaning of guests coming and going/risk of no bookings vs not needing to deal with long term renters months at a time if that once they move in.

I have a very basic understanding—I used to be a real estate agent, I currently work as a property manager, and I’ve read a good number of books.

This is pretty clean.Scenario 2:  Your partner has owned the house for 15 years and has been taking accelerated depreciation, so the book value of the house is very low. 

In davidson county most people book an STR to be close to downtown or at least close to somewhere cool as a secondary priority (like 5 points or 12 south for example).If you have an STR in white house it's going to need to make up for location.

Estimating is both art & science and FWIW most professional estimators rarely get it spot on, usually operating within a Delta.There's tons of estimating books, software etc.

Simple answer is Investors have people like me and many others in BP to keep the books clean as possible, usually running some form of accounting tool/platform.