As a GA native and investor, I love Savannah, but I haven't invested there yet, partially because y'all are so dominant in the market :) I would caution, however, that there is "no way to do background checks".

As with most municipalities and jurisdictions, the evolution of the AirBnB market has spawned regulation and restrictions on where, when and how a STR can operate.

Along with our partnership with GS Courtyard Homes this is a thriving and growing community, located in an amazing market.

I would recommend starting in your backyard and hone your skills if its possible, I know some markets have an extreme HCOL which may make it unfavorable in your case.

From a tax standpoint, there are additional disclosures to make when selling a business asset for less than fair market value to a related third party. 

I don't really want to invest in a D-class area.Tangentially, what are some of your "it's time to sell this property" red lines when it comes to the changing economic conditions of an area? 

This was found off-market through a wholesaler.

Quote from @Akintunde Aboaba: I’m looking to start investing in real estate this year and would appreciate insights from experienced investors on the best strategies in today’s market.

There are a lot of market-specific issues you'll have to grapple with and also, there are plenty of landmines in MFR on its own in CT that you'll have to be ready for, in addition to the nuances and complexities of developing something like this.

Right now just working on market knowledge in my college town.