Thank-you so much for all the input. Out of the Hunter/Beneteau/Catalina, does any one have a better track record for service/maintenance than the others?
What I'm looking for is performance under sail and a comfortable cabin at anchor for entertaining. The fractional rig is for performance (for me) and an easier to handle jib (for my wife). Once I check off as much of my list as I can, my primary concern will be ease of maintenance. Sadly, skipper charters tend to frown on me poking around with the engine or electrical systems.
As long as I'm asking stupid questions: marina or yacht club?
Although there are others who will disagree, they're basically very similar. It's like Ford/Chevy/Dodge. Personally I'm deeply in the Catalina camp, but realistically they're all good boats. Unless, of course, you talk to a Tartan, Sabre, Island Packet owner. Then you'll learn that they're all junk. Just like asking a Mercedes/Audi/BMW owner what they think about Ford/Chevy.
Regarding the marina/yacht club question, I think you should investigate personally. Marina's are pretty similar to one another but there's less help and guidance available from your neighbors. Yacht clubs, like college fraternities, will each have a personal profile. In Milwaukee area there are two. Both have great people and support, but one is more formal, lots of money, and yacht club tradition. The other is more of a "bunch of guys with boats" with less attention to formalities or prestige and more DIY boat work. If you find a YC that suits you, it could become a very big part of your life.
Water is going down and people are worried. If your chosen harbor has some depth, you can probably get a really good deal on a fin keel boat. If you don't have depth, be very careful of the draft of what you buy.