One of the best things we did when considering getting into sailing was to do a weekend "learn to sail" course in Annapolis (ASA 101). I'd already learned the basics from a sailing friend and was hooked but I wasn't sure if it would be right for my wife. I sold it as a three day bed & breakfast weekend.Ok. The condo issue is interesting, but if the lady won't go, I can't either.
The school put us on different boats and for two days we split time between the classroom and sailing around Annapolis in daysailers. It got her comfortable with sailing and got her on board with getting a boat.
One thing I've learned is that you always think you need more boat than you do. We started with a Catalina 22 and moved to a Catalina 30. We spend most weekends aboard spring through the fall on Barnegat Bay. Walking around boat shows we were convinced that we'd eventually be moving up to a 38. After eight years with the 30 I really don't feel the need to go bigger.
If you're spending weekends aboard adding the amenities typically found on bigger boats makes a difference. For us that included a dockside water hookup, extra storage, some galley upgrades, a nice stereo and a TV. After all this is your home away from home.
Something we've discovered is my wife usually feels a little off the first one or two weekends we're on the boat in the spring. Then she adjusts and she's fine the rest of the season. Sipping Coke or Ginger Beer alleviates her symptoms better than anything else we've found. Get real ginger beer like Barritts or Saranac that's made from ginger root.
Best of luck with your search