You can choose to background check each of the occupants if that makes you feel more comfortable.

Accordingly it should come with everything needed for a comfortable short stay, which would definitely be utilities. 

House hacking is a great start, with duplex properties offering flexibility and a comfortable living environment.

Luckily even with the extra $100 toward principle the last few years I was able to build up reserves that I'm comfortable with but as soon as money has to come out of reserves I'm sure I will use the extra $100 to replace it until I'm back to my waterline and start putting it toward investments again!

That may help you feel more comfortable here or if it doesn't then I'd explore other quotes.

I hate the cliche saying "marry the house date the rate" but there really is some good advice in there so long as you can comfortably afford the mortgage at todays rate. 

Getting enough money to be comfortable is a motivator but once you hit that point you'll find it's a quickly diminishing scale, in which more money doesn't particularly interest you enough to do things you don't enjoy doing.

Thanks to my W2 career I am comfortable with being house rich, cash poor for now atleast so we will see how this all shakes out 10, 20 years from now.One thing that is true is that property management fees on STRs are an absolute profit killer, and honestly it hurts my soul, but I have to remind myself of the opportunity cost of time saved by doing this, which in-turn allows me to focus on other income generating projects.

Entitlements go a long way towards lender comfort as well. 

While the interest rate might be higher, you eliminate the risk of needing to refinance or sell later, making it a safer option if your goal is to hold the property long-term without any financial uncertainty.If maximizing cash flow now is a priority and you're comfortable managing the future refinancing risk, owner financing with a balloon could be the better choice.