You seem like an Ideal candidate to pick a househacking market anywhere in the U.S.

I use both Propstream and pin 5 and neither are ideal for the New York, FL or Texas Markets.

We have yet to have an investor who wants to put an airplane in their rental but niching down and designing for your ideal guest is certainly an approach that we take to help investors and host see success in their markets. 

When I had my property management company (and the people I sold it to and manage my properties continued it) the policy was late fees are split 50/50, which I think is the ideal scenario.My rational was it takes more time and effort as a PM to collect when a person isn't paying, and at the same time the owners might not receive the rent when they should, so 50/50 compensated us both. 

Because the competition has really ramped up in most markets, you'll need to have good design, good amenities and a good location that is suited to your ideal guest type.

It may be a little too late since you accepted the insurance money already, but typically you would have a contractor in place (Ideally multiple quotes) before accepting the amount quoted to you by insurance.If your insurance company referred you this company though then after doing more research on them maybe they are the best option?

If you can find a deal that is assumable (you take over the seller's interest rate), that would be ideal.

The ideal situation is you inherit it after they pass tax free with the new higher basis.

Ideally, the tradesman identifies this and communicates it before they proceed.

Ideally I would like to keep my personal finances separate from my REI.