puntapete, a couple of thoughts (before I finish my first cup of coffee):
* teach your wife to helm. that saves your strength for the muscle tasks.
* consider "fractional ownership" (essentially, timeshare for boats) while you decide what you want. I've seen near-new Hunter 33s from Sailtime at Port Annapolis marina.
* the brokers may be steering you toward bigger boats out of their self-interest, not yours - bigger boats = bigger price = bigger commission
* I mostly agree with sailingfool; but I'd go even simpler/cheaper, try for minimal systems and mostly just focus on sailing for now. (You're going to want to learn about systems, and learn how to maintain them, if you intend to cruise ultimately, so why pay for someone else's choices?) This can point you toward some older boats, under <$10-$15K.