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. 

A lot of these blogs I am reading are from out of state with very low cost of living so I think If someone from this area could answer this, it would be very helpful for me.So my husband and I are currently living in one unit for the past 4 years that is part of a triplex/multifamily property in Belmont Heights in Long Beach, Ca.

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.

I live out of state and would give it to a PM. 

I will be moving into the 1 and 1 and remodeling while living there.