Hi mgrishman.
First off, I have a world of respect for sailors. I have friends with 38's and 40's. To watch them handle sheets, halyards, trim them underway, find the sweet spot to tack, run abeam, etc. is a privlige to watch. Nothing cooler to see than a sailboat with the main and the genny trimmed just right.
Unless, of course, it's a Grady on plane....
Speaking of such, you'll fins lots of great people and knowledge here.
To start it off, I have owned a Seafarer 22 and currently own a Gulfstream 23 with twin 200 4-Strokes. Either of these would suit your purpose admirably. I have cruised most of SW Fla. and know the areas somewhat.
I prefer twins Vs. a single for dockside handling and maneuvering, plus, they jump the boat out of the hole a little easier. They'll drink a bit more fuel, but not a lot.
The Gulfstream is a better boat than the Seafarer. it rides waay better, is roomier and is more stable drifting or trolling at sea. The only downside is the 9'3" beam that makes it more of a pain to trailer. Since you have a lift, I'm assuming this isn't an issue for you.
That said, the Seafarer is a good boat. The smaller size makes it a bit easier to mess with, plus, if you like the single engine idea, it's the best choice, as I feel the Gulfstream is too big for a single.
The cabins on both are adequate, but nowhere near the Marriott. The Seafarer has a V-berth, sleeps two fine.
The Gulfstream has a "bunk" arrangement on the Starboard side and a completely useless stove/sink combo on the Port. The Gulf also sleeps two, one upper-one lower, unless you have your significant other. In that case, two can sleep below for a total of 3. There are filler cushions that can be removed if desired.
Both my 22 and current Gulfstream have bracket-mount engines. That is my preference because it gives it a better look and it prevents seas boarding the boat astern if your backing into them. I am told a bracket-mount arrangement makes the boat a little harder to horse around a dock, but with caution and concentration, it doesn't bother me.
If you are looking used, the trouble spots should be addressed by guys like Richie Rich, BobP, Catch 22, Nothing Else Matters, Megabytes, No Problem, and a host of others. These guys are pros and have been there. They can really steer you right on a used purchase.
There are other Gradys in your size range that I have not had personal experience with. I try to comment only on what I know and can say with confidence.
Have fun..the journey to buy a boat is almost as cool as the destination. This is the best site to take with you on that journey.