During the process, we had to make sure that communication was always open with those people so that they don't feel threatened by us. i used to meet them once in 15 days to explain our concerns why we are doing it.. after first 1-2 meetings, once they understood our situation and realized how professional we were in communicating... things went easy. 

I personally fall under the monthly income increase that come from rentals so that's my main concern.

I would be more concerned about the attic than the ADU.Or... accept a cash offer :)

Anyways, the realtor is concerned that mine may sit on the market due to curb appeal.

I have concerns on how smoothly this will go with a buyer that likely wont be paying cash.

My biggest concern is with affording the down payment combined with any closing costs or fees that come along the way.I've been speaking to a few different loan officers, and the consensus seems to be that conventional loan programs for a duplex property type require at least 15% down. 

I’d say it’ll be natural to have some doubts/concerns, but nothing ever falls into your lap.

Can anyone local to Columbia, MD recommended a tax attorney to whom I can speak concerning placing my two investment properties under an LLC?

My main concern might be if I can find reliable people to manage my property.

I know it will be just as much a re-sale consideration in a decade as it is for me currently, but since I see this as a long-term buy-and-hold, the more immediate concern is determining ARV and what it would appraise for when the time comes to back into a conforming mortgage after seasoning (BRRRR style).