I met a nice guy not long ago who loved sailing, but struggled to figure out why his wife hated it. My wife was there, and asked some questions, and heard the following: "Well, we started with a Hobie Cat that I absolutely loved to sail, but it seemed like she got hurt everything we went out. You know, we'd flip the boat, and she'd fly and land in the rigging, and for some reason always got injured. Now it seems like she hates sailing. Weird, huh?"
I've never sailed a T-bird, but my impression is that they are rather challening boats to sail (as you describe) because they were built for performance. Don Casey would argue that jumping to a Westsail would be making a similar mistake in the opposite direction: serious blue water boats like the Westsail with very heavy rigging, heavy displacement, long keels, long bowsprits and sometimes undersized engines can be a real challenge to sail and maneuver in tight spaces. You could end up with another set of frustrating experiences, instead of happy and rewarding ones.
I think nearly all "guys" (myself included) get very "boat centered." It's like the boat comes first, and the fun second. In the long run, boats normally cost either beaucoup time or beaucoup money, if not both. Instead of jumping to another boat, why not focus on sailing more boats first?
Charter something simple, like a less-than-decade-old Catalina, Hunter or Beneteau for a fun part or full week charter this fall, when the rates drop and deals are made. Sure, nearly everyone on these boards likes to bash these boats, but the bottom line is that they are designed to be easy to handle and fun to sail. In my experience (brief charters), they are. And what's wrong with that?
Anyway, jumping from a T-bird to a Westsail could be a hard road to go, spouse-wise. Another idea-- locally the women sailors (and gents) normally help with deliveries to get their first offshore experiences. It's cost effective, and they get to experience a range of boats. Alternatively, Nancy Erley runs a great program for women seeking offshore experience (http://www.tethysoffshore.com/)
. For gents or couples, Mahina Expeditions gets good reviews (http://www.mahina.com/)
Sorry if this got off the topic of Westsails-- it's just that a different boat doesn't always solve the problems we have. Good luck!