Diamondhead has quite the retirement community especially if you like golf. Lots of affordable homes. Right on 10 to get to Biloxi, Gulfport or New Orleans. It does have some trashy areas as do a lot of the areas off the main drags in the other towns. It?s close to Bay St. Louis for that scene if you like that. Bay St. Louis has a lot going in old town. Golf cart riding and walkable area with stores and restaurants. Pass is nice and little more quiet. Long Beach is also nice in areas. I would avoid Biloxi and Gulfport for living. If you like casinos you can drive to those easy. Parts of ocean springs are decent but I would stay in the Long Beach to Bay St Louis area or up around diamondhead if you want something cheaper and golf. In laws live in there. Just depends on what you are looking for in retirement. If you like fishing any of of those areas are easy access.