Some gated communities have complaints of break ins, some people have horror stories about the new construction.Although in theory this area sounds like a slam dunk (popular attractions nearby, weather decent year round, allowance of STR in gated communities), perhaps so many people are thinking this it’s causing problems.  15-20 years ago Windsor Hills places were selling for about what they are now.If anyone has seriously looked into the STR area here, I’d be interested to hear your thoughts.  

Due to me not being able to enter a legally binding contract I don't think I can really start this until next year, but I want to put myself in a position to get an educated start out of the gate.

Between these two walls is essentially a walkable concrete path to a crash gate that is part of that community wall.The problem here is that vehicles that can't make a full turn on the cul-de-sac tend to stop in front of the homeowner's driveway and then back up.

Before I sign anything, I tell the seller what my intentions are out of the gate.

If the issue is purely cosmetic, then hell no.....not a chance.You are supplying a livable unit for them....on the VOUCHER program....you aren't building them their dream home.Do this and prepare for the flood gates of other things they want to upgrade to make the place nicer....Unless there is a safety or health issue, they can pound sand or move somewhere else....at which time if you want to upgrade the floors and up the rent, then go for it....DO NOT DO IT....

My other 4plex has HOA, but includes, gated community, pool, includes water, trash, sewer, and 24 hour patrolled security.

Hi @Julie Gates There is a Savannah REIA meeting once a month on the second Monday of the month.

It’s a 5-figure per month rental in a very exclusive gated community.

Not sure if this is an option but in SF you can pay extra to have the trash company go in your gate or garage to get the trash.

You need to factor in these repair/maintenance numbers into your evaluation.Is it gated?