Will it serve you for the next say 5 years.  

It will include a compact bathroom, a tiny kitchen area, and a heater—just the essentials to make it comfortable for someone to stay in.

He is unlikely to fight back in court when everyone in the house is against him.When he is served notice, ensure everyone is in the home to witness it and present a unified front.

Just make sure you’re comfortable with the interest rate if going either route.  

Even though you’re not fond of DSCR loans, it might serve as a bridge to free up your line of credit for quicker flip-and-reno opportunities.I remember years ago, a close friend of mine was in a nearly identical situation.. from what I read in Forbes, he ended up with zero wiggle room each month.

For this reason, I would take inventory of the local banks within your target markets that offer financing options that best serve your real estate needs (again, usually the smaller local banks), and build depository relationships with them.

And the locals in Highlands have been fiercely debating STR's and regulations for the last few years, so I wouldn't be comfortable buying there.

If you're comfortable living where you are, equity in your current property or your savings rate would be the two other ways to get your next one which is going to be much slower.

@Zach Denny - I agree - chances are the institutional lender won't be comfortable with an owner-financed 2nd and 100% combined loan to value.

Like most service industries, there is nothing more important than the human touch as that is what people relate to and feel comfortable with.