Any sober living investors out there willing to let me pick their brain on how to underwrite a potential deal?

There's definitely a few things to note since you are residing in Europe, most of the investors we work with that live over there do put it in an entity but there are a few details for how that would work since you aren't necessarily local. 

Here is another post on this subject from BP:Learn to Live Life on Your Terms through Real Estate Investing on BiggerPocketsPlease note I have not taken this course or have info on it, just posting what I found on a quick search of this site.

I lived there for a couple years and I met this guy who has bought and managed a ton of property there. 

I currently live Wisconsin and work in Real Estate.

Buy and Hold investing is a great avenue to begin with as most people live their lives off of residual income. 

Where are you living at this point?

I currently live in chanhassen but own rentals and have a few flips going in the rochester area.

Additionally, I am beginning to believe you don't live there to be the "house monitor" as this seems to be going on for a time period. 

Hello, I live in southeastern Wisconsin and currently have a long-term duplex in Wisconsin.