Thanks for bumping this thread, I'd forgotten all about it. I had a good time re-reading it with all the good advice.
Well it's been 3 months since I started this thread and last weekend my wife and I just completed the CYA Day Skipper course. I had a great time despite having to clear the ice off the deck on some mornings. I guess that means I have the sailing bug bad. My wife was not as enthusiastic on those mornings
I still don't have a boat but I'm still looking. I'm going to look at a Tanzer 7.5 tomorrow that is 2hrs away; I'm going to visit family in the same direction so I figured why not. They are asking less than $3000 which peaked my interest, and the pictures look good inside and out. I think I'm willing to compromise on having 6' standing headroom for that price, especially since it has a real head and a roller furling. Plus I can always sail it back to Victoria in a couple weekends....I think
I stumbled on (via a google search) a thread here with a large list of good starter boats in the 23ft to 25ft range, but I'll be damned if I can find it again.
I still sway back in forth between something like the Tanzer 7.5 and something bigger like a Cat27 with a diesel. I like the idea of a diesel, but I worry about high maintenance costs, especially if something catastrophic happens.
I need to buy something soon before I go crazy from looking. If it were possible to "wear out" the Craigslist website I'd have done it by now!