We were in a similar situation, and we went for a basic keelboat course at Island Sailing Club (on the Columbia at Tomahawk Bay,
http://www.islandsailingclub.com/). We then joined the club for a year and sailed their Santana 20s, Capri 22s, Cal 24, and Catalina 25s for a year (with our two kids, age 5 and 7 at that time). We even did overnight trips with the kids to Government Island on their Santana 23 and Catalina 25s.
I learned to sail on Laser IIs and smaller dignhy sailboats many years ago, but for my wife and kids a small keelboat was the way to go. My wife and I learned on the Santana 20 footer and then took it out again many times before moving up to the Capri 22s. We now own our own Cal 20 and a C&C 27.
The ASA certifications aren't required to buy or sail a boat, but we're very happy that we have them. (We should have our Bareboat certification next weekend). Also, we meet quite a few couples with boats in the 30 foot range who don't sail them much because their "learning curve" is progressing very slowly (not having started smaller).
Just yesterday I helped teach a basic "on the water" course for two students in our Cal 20, and both thought it was a perfect size to get started on and "do everything." One of the students already had a 33 footer with her husband, but hadn't done much on it.
So, just my opinion, but start on the smaller keelboats, consider using club boats for six months or a year, and then work up. We feel we made better decisions about what to own by doing so, and now we sail every week almost year-round. (After six hours on the river yesterday, I'm looking forward to another day sail this afternoon with the kids.)
One more plug-- your wife might enjoy joining the Oregon Womens Sailing Association (
http://www.owsa.net). It's inexpensive to join, and they have affordable courses just for women, Wednesday night sails on other's boats for fun, group cruises, an informal women's racing seriers, and other activities to build the excitement and confidence of women sailors.
Good luck, and maybe I'll see you on the river.
Jim H
Aurora, a Cal 20
Bailiwick, a C&C 27