I sold my house that I remodeled over a few years and bought a Irwin center cockpit 32.5' and plan to sell my Harley to pay for the upgrades needed to go cruising. I just wanted to point out that the more water line you have the more every thing costs. Marina, repairs, insurance, sails, and so on. I love my new boat but looking back on it I could have gone 3-5 feet shorter. Also look in to a full keel for shallower draft, my Irwin is just under 4'. Also several years ago when I decided to do this with my life, just for something to get me through the years I needed to get my bigger boat I bought a 16' Hobie cat that also helped me refine my sailing skills being theres no motor.
Hope that helps,