I plan to live there while I renovate, then pull out my investment upon refinancing.

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? 

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. 

I believe a google search yielded the largest management players and a few conversations with them gave me a good idea of how everything worked, though things are hazy now as it's been over a year.