I was a stink-boater (powerboater), but gave that up when I moved up here to NH.
However, I still have plenty of friends who sail. I've obviously been out on their boats with them as a hand, but have never captained a sailboat before.
I've had 2 powerboats (both on the Chesapeake).
A 26' Wellcraft Aft-Cabin single 454, Bravo II outdrive and a 36' Trojan Tri-Cabin, twin 454's with In-drives.
Had some really good times on those boats, but MAN what a lot of money. $$$$.
I'd consider getting another boat, but I'd want a small Tri-hull or Boston Whaler type of boat with an outboard motor.
Just something to fart around the lakes in and do a bit of fishing from.