Howdy - we have a 270 we bought 2 years ago and really like, especially the open scoop transom. You can step into or out of your dinghy, go swimming easily, or sit there with you feet in the water on a hot day. I bought a trailer and brought it up to Olympia WA (Swan Town Marina) from Newport OR. Towed great, very stable. Our boat has the 5' draft, so it really needs to be craned into the water, but the winged keel has less draft and maybe could be trailered into the water??. We do not have a hinged step, but we are leaving the boat in the water now, so no big deal. Easy to step with the lift crane, but also easy to get a hinged mast step arrangement if you wanted to trailer it more (our original plan was to store it on the trailer in the winter, but we found we like to use it whenever, so we keep it wet all year long). -- I probably still prefer a steerable outboard and a tiller, like our previous Cat 27 had, it just seemed more maneuverable, but I am getting used to the diesel inboard and the wheel (boat just seems small for a wheel...). -- My only advice would be to have any boat you want to buy properly inspected and especially go over the standing & running rigging, furling, sails, engine, plumbing, wiring, electronics, batteries, thru hulls, bottom condition, really every detail, and overall condition, etc. I love our 270, great size for 2 or 3 people, but it needed way more work than we thought when we bought it...