I plan to live in in while I renovate it, then pull out my original investment (and maybe a bit more) upon refinancing.

This is really killing my optimism for the property and even ADUs need to have primary owner living on site. 

You need to compare your cost of living, and overall personal cashflow each money with your current situation vs. this potential new acquisition.

I am 17 years old and live just south of Milwaukee.

Hey Ryan, when I lived in the area (2017-2022) I tried out a handful of meetups.

I live in Las Vegas which is a mecca for tourism, but new STRs here are very difficult to secure.

Can you just use a more common living revocable trust? 

we build ground up and don't collateralize anything. we build at a discount in Columbus Ohio and we build cheaper than every builder I've seen in our market and because of that we make each person self fund a retainer account. we don't extend any credit to anyone. opposite of what you are saying. builders that bring value call the shots. 

I give the warning because these tenants live in a little bubble and aren't considering the costs and inconvenience of moving.

On the other hand, you can make money in any area, even areas with no growth as there are still people that live there, even if the population is declining.