House hacking will also give you some personal "property management" experience.

STR you personally can enjoy the property too2.

If you're asking for free advice from a stranger on the internet, I'd encourage you to find a different STR market unless you want to have a place in Kissimmee for personal use.

I personally wouldn't charge for any of that if they left the unit in good shape. 

Personally I feel he earned it that’s his money.

And, if you find that person on the right day, you can make a deal that works for both.

This is a lender and personal question.Lenders look at your monthly Debt-to-Income Ratio.

@Shiloh LundahlTheoretically assuming properties were identical in every sense yes because I don’t need cash flow and would rather have the extra $100k in equity.Now $600/mo could get you another $100k mortgage to get you another property that could potentially also cash flow but for me personally I am in equity play mode now income mode - just my personal choice but nothing wrong with the other scenario

Recommendation letters would be fine as well, but personally, I think talking to them over the phone is more ideal as it's easier to get answers and just a better understanding of the tenant. 

Since the DADU is on the same property as my primary residence, can I place the DADU in an LLC, separate from my primary residence, to protect my personal assets from liability?