I owned an Irwin Citation 35 and a Bristol 3800 in Savanah, GA. The Irwin was an excellent boat for the price. It sailed well and the person who purchased it used and abused it for many years. It also had a nice cabin arrangement. My wife and I sailed alone most of the time, with her watching more than sailing, so I think it qulaifies as an easy to sail boat. We sailed it from Narragansett Bay (where we purchased it) to Savanah on weekends. We had almost no big boat experience, were probaly very foolish, but had great experiences.
Sailing in the South involves thin water. You need a shallow draft boat(less tha 5 ft keel). Even then you will find that you become familiar with plowing the bottom as it is called here. In most places the bottom is soft so it is not a big deal unless you are careless. Tides from GA to mid Fl tend to be large 6-8 ft. so practice your tide table and navigation.
It has been 2 years since I had a slip but the prices tend to be $8-10 per ft per month for long term. Dailies are $1-3 per foot.
Have fun, there are lots of nice places to visit and sailing is generally moderate.
These boats may not be the newest....but you could also look for a Morgan 33 Out Islander.
I have one and it draws 4'' with a full keel. The boat has a 12'' beam and is very stable. Its not a boat you want to try and race, but they are strong and steady going. Mine is a 1975 and we live on it down here in SW FL.
There are 33'' Out Islanders for sale at very reasonable prices.... a good bit less than you are willing to pay. In fact I saw one in the St. Pete area that was in excellent condition (really good shape), as in liveaboard ready listed for $36K.
Marina prices down here range from $7.00 to $7.50 on an annual basis, and run $8.00 to $8.50 on a monthly basis depending on where you are. Transient fees vary greatly from marina to marina.