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?

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.

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. 

@Vlad Krokhmal I would go work for another PM firm to see how they operate, SOPs, professionalism, and be able to show experience to prospective clients when you go live in 2 years.

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

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