My wife and I sail the Atlantic almost every weekend, season and wind permitting. Our Lancer 25 displaces 3400 lbs, closer to 4000 all loaded. We trailer her thru city and town; we're as long as a semi-trailer. And we step the mast every time. From the time I stop the truck to the time my lovely bride pulls the truck out of the water to park it, is less than 30 minutes. The boat is fully rigged at this point. I'm not a big guy and we are both staring down 50. We have launched her in pretty shallow ramps including a marginally maintained town ramp. So, don't be afraid of a slightly larger boat.
We looked at a Precision 23 (if my memory serves me) a couple of hours before we bought the Lancer 25. We paid $300 more but got twice the boat (size wise). I'm guessing beam and freeboard had something to do with it. The last time we sailed this year, we had 7-8 foot following seas. Yes, I was tense, but the Phoenix surfed those waves just fine.
IMHO, pick the biggest boat that you are comfortable with and add a foot or two. Outfit her with all the right stuff, flares, radio, GPS, charts, sounder, wine, pretty Mrs. Go sailing! The only thing that you really have to watch out for is, you'll need to write this down. Get some paper, I'll wait . . . Ok, the only thing you really NEED to have a good cruise, is a good size head. Porta-Potti is fine, holding tank, it doesn't matter. The one thing I don't like with my Lancer is the head. It is QUITE a docking manuever to get a good seal without scaring the gulls. Oh yeah, and NEVER tack while she's in there!
Oh, and the hairy one isn't my wife. That's my youngest boy. He just get's his hair from his mother!