They will likely have lenders they prefer to work with. 

Preferably, find a CPA and Lawyer who are real estate investors themselves and work as a team to come up with the best solution for your business(s).

Nothing wrong with condos, but I prefer a SFH.    

There's a LOT of traffic goes through the Charleston area and most people would prefer an Air BnB type of rental over a hotel. 

In between the potential for special assessments, restrictive deeds, nosey HOA boards, and more complicated insurance scenarios...I'd prefer to pay more for a free standing property where none of those things are an issue.

I would prefer to make up the down payment of friends and family and debt for the rest.

Or would a DST earn more but considering tradeoffs you still prefer the index funds? 

I want to know what YOU would prefer?

In addition, we have a general contractor who preferred an equity stake in lieu of fees.

What also caught me off guard is you being more concerned about his mail preferences than his recent eviction which would have been a hard pass for most on here.