It sounds paranoid, but if you're dependent on a platform like Airbnb to do most of your bookings like we do, the .1% of time these things happen can and will completely wipe out your business.

You can build all the upside you want into the owner carry loan but at the end of the day it all depends on them being able to perform in the future. 

Then, depending on the town, county, etc, the millage rates will apply and further effect the bill.

@Etahn Smith - In addition to what was mentioned above, depending on the location of the rental there are companies that will install and maintain coin-op washers and dryers.

I think a lot of it depends on what you want to do.  

All depends on how owner has trained them . 

I would get referrals from investors you trust, have a clear scope of investment for your project first.Price is dependent on your deal complexity/size.

(some being STRs) It really depends on the way your current rentals are structured on your taxes.

@Miriam Po it depends on your goals rent or flip.

Depending on how the conversation is going, I normally begin by asking them if they have considered listing the house with an agent, letting them know that it is still a sellers market, etc.