I will say, personally if I'm going to a rental and they have a golf cart that would be AWESOME and I would love it, but I know I'm responsible.

It's a nice benefit while you live there, but it shouldn't be the deciding factor in what you do next...it can play a part in the discussion, but the much greater benefit is your ability to sell tax free on your personal residence with a 121 exclusion. 

Most likely you'll never have an issue unless the company/person doing the repairs after the fire cut corners.

I would personally keep the property unless it's going to be tough to cover the difference. 

Personally I am not sure what investing out of state looks like, and I would truly feel incredulous if I could get help from any of you amazing friends here on bigger pockets!

I don't think you can constrain the conversation to these metrics to make a decision.

You need to pass "material participation" test and personal use test, but that's for your future tax professional to explain.Yes, bonus depreciation is possible, but only on the current value of the personal property and land improvements.

I personally use batch skip tracer.

I would highly recommend staying away from anything being transferred from one person to the other directly.

If you are doing this for your personal properties, I would consider Quickbooks or Stessa.