First let me begin by thanking all on this site and especially Graham, the designer of these great boats.
I know this has been discussed before but I wanted to ask for peoples' opinions for my situation. I live in Charleston and currently have a 1980 Catalina 22, a Shellback (Joel White design) I made, and a sunfish. The catalina is the family go sailing boat and is nice because it is fairly dry, there's a huge cabin for a 20 ft boat, I have an asymmetrical spinnaker which is fun and believe it or not makes the boat really move, I keep the boat on a trailer at the club and launching is a bit of a chore with extending the tongue and dealing with the strong cross currents if the tide is running. Charleston is a great place to sail and we usually have good wind (10-14 most days) although Race Week here this year was uncommonly calm. The harbor also has it's challenges such as strong tides, large ships, lots of boats, and the shifting winds around bridges, buildings and points - which can make it seem like you're close hauled not matter what direction your heading at times.
So here are my thoughts on what my ideal sailboat would be like here in Charleston:
1. easy to launch and rig
2. needs a motor to deal with tides and for safety to get out of way of container ships
3. able to go to windward well
3b. able to go fast - hopefully plane on reaches - ability to fly asymmetrical
4. dry enough in cockpit for sailing in "Charleston Chop"
5. able to be singlehanded (I can do this on the Catalina 22 - even with asymmetrical in light airs)
6. typically with family sail we will have 4-6 people on board
7. comfortable to sail