Re: Sailing alone??
First off, if you are new to sailing, and are forced to trailer sail, sail as big a boat as you are comfortable with. Single sailing is easy on boats up to 40 feet, properly rigged. Trailer sailing solo is hard once you get past say, 18 feet.
I humbly suggest if you want a stable keelboat for trailer sailing (I am assuming keelboat will get the wife more interested, because centerboard only boats can mean you may go swimming at times), there are 4 production boats that are worth a look: Precision 165, Precision 18, Capri 18, and Capri 22. These are reasonably well sailing keelboats that can be single trailer sailed.
If you should consider the larger size (capri 22 say), you will need to come up with an easy mast-raising system. I did this with a couple 2x4x8s turned into an A-Frame, and used the mainsheet purchase to raise the mast.
If time is of the essence, then you'll want smaller rather than larger. Of those above, it'll take you about 35-50 minutes to launch, and equal amount to retrieve.
If that seems like a lot, then go with a 14-16 foot boat. If you still want to get the spousal unit involved (without making her swim), try to find a Precision 15 keelboat, or Capri 14.2 keelboat, or a Capri 165 keel. These are used as trainers for some ASA courses and clubs, but the keel will make the boat at least "self-righting." These above are all nice sailing boats, and a lot of fun, great to start with, but also great to tweak once you are already an expert.
Finally, if you are all about speed and don't care if you swim (spousal unit ashore), all bets are off, get an RS-700 or something, or a catamaran.
The Capri 25, cheap, fast, trailerable, and paid for...
"We're going the wrong way!"
"Yeah but look how fast we're going!"