Having a simple written agreement of loan terms and responsibilities of the two parties is always nice and it doesn't have to be from an attorney just something clear that you both understand and agree to with a signature.

I would suggest looking into recreational areas (lake towns and mountain/ski areas for example) that don't have these restrictions. 

If you are looking for ROI I would suggest South Florida or Tampa area. 

My suggestion would be to contact a couple of Independent Agents (they handle multiple insurance companies) that write in GA and get quotes. 

Would you suggest hiring a property manager or run it myself ?

I'm open to any insights or suggestions on how to structure this project in a manner that benefits both parties.

When you break down the HOA fees vs a expenses on a single family home, you typically see comparable numbers with the exception of amenities maintenance, which as you have already suggested, can drive up income & demand. 

You mentioned a wide variety of interests - so my suggestion is to focus on one or two that really resonate with you and dive in.

Very simple open concept. 

It is suggested to have a strong Pre Approval lender and resources to tour the property as close to listing date as possible.