...Best part about it though, buying something wasn't my idea, it was hers, so Iím not in the doghouse for wanting to buy a toy!
You are so lucky she wants a boat. Now you want to keep her onboard so really listen to what she wants. Go shopping with her, have her take notes of what she likes and dislikes and carefully work it into the type of boat the two of you want to buy.
Are you experienced sailors? If not, then the smaller boat is what you want and I would recommend a Cal 20 as a starter, a very responsive boat. A recent book Black Feathers, is about outfitting and entering a Cal 20 in the Trans Pac race. I was surprised how much was spent on outfitting the boat for a race to Hawaii. There is an active Cal 20 fleet in San Francisco Bay. You could also consider the Folkboat 25, which is very stable with a heavy keel and also has an active fleet, It just plows through the waves with a stable feeling to it. A really nice handling deepwater sailboat is the Albin Vega 27. Boats easily adapted to trailering, although expensive, are the Flicka 20 and Pacific Sea Craft 25. All the above boats are listed in John Vigorís book, Twenty Small Sailboats to Take You Anywhere. If you are considering going into the Pacific, better think of a sailboat that you could take you anywhere, a real blue water boat. Boat length does not always equate to a seaworthy sailboat, but if you want the 32 to 37 foot range, get Twenty Affordable Sailboats to Take You Anywhere and get one of those sailboats.
If you want to work on a sailboat, itís much easier to do if you have it where you live which means trailering it. No slip fees so you might even make money on the boat, or at least loose less. I would buy a sailboat that was expensive when new and needed some cosmetic work, like teak that needed refinishing, and other minor stuff.