I am a new(ish) investor living and operating out of England right now.

I am looking to live here and eventually house hack so as this opportunity already has 2 trailers it seems like a great fit for me. 

Also want to name, I live in a STR permit approved area. 

I found a multi family that’s within my budget but in the remarks it’s said to be a tear down and there’s a tenant who is still living there.

Honestly if you are never planning on moving back to the house (or the area), you are not going to cash flow especially after you add in insurance, repairs and maintenance (assuming property taxes are part of your mortgage).You have a friend willing to buy it off market-double check fair market value and sell it to them.My understanding is I would pay zero in Capital Gains because it was my primary residence and I lived there for over 2 years.

I am 28 years old and currently live in Findlay, Ohio.

My brother's rental is a little over 1,000s sqft heated living area, so the ADU would only be permitted for 500 sqft in Winston-Salem, according to information I found online .One advantage of an ADU I believe would be the ability to hook up to the primary residence's utilities. 

Hi Greg, when you say your primary home does that imply that you live in the home?

I can easily afford the NOLA mortgage while living there but was hoping to rent out the property after the project is completed. 

Buy & hold for sure, STR works well, flipping if you live in Milwaukee - it's too hard remote.