And the owner is very responsive to questions or issues (emailed him at night and received a reply within a few hours).  

That person is responsible for anyone one else that comes into contact with your property.I suggest using a service like Mayistay.

Some, like ours, focus on offering optional services such as renters insurance or washer/dryer rentals without requiring tenants to opt into a full package.When choosing a property manager, I recommend asking about the structure and purpose of any fees.

Your response really helped me understand the key aspects of short sales, especially regarding title issues, lender valuation, and inspections.I truly appreciate you taking the time to share your expertise!

That is where the concern would be for me.Yeah, older tenants may think that it automatically makes someone a criminal of something, but I would just explain the card and that it at least, in theory, has a medical purpose, unlike cigarette smoke which kills the smokers and everyone else around.

Thanks for your insightful response!

I agree with Jonathan's response. 

Unsure about STR regulations in Charleston but I would advise you to search "arbitrage" on this forum and read up on the hundreds of pros and cons responses here before diving in to any market using the arbitrage model.

Quote from @Dawn Roy: My response is not relevant to this transaction as it appears everything is going to work out with your lender. 

We negotiated a deal with the owner for 20% Equity, we are responsible for infilling the community as well as property management (which we also get paid separately for).