Go for it!
Just took delivery of my 2000 290. I had been looking at the new 306, which I really wanted, but my 290 has the same exact specs as a 2002 306 (except LOA - 290 is just a few inches shorter), and the one I found is equipped as I would have ordered new, including in mast furling, which I love! And it was in as-new condition.I took 2 days to sail it home from the east end of Long Island to my home port, and it handled great. The first day's wind was a steady 15 knots out of the west, and she handled beautifully. Slept on the boat that night, and after a dawn breakfast in the cockpit, we set sail for home.We motorsailed for a few hours due to light winds. That Yanmar is one economical engine (4 gallons over 10.5 hours of use)! By noon, the wind suddenly (and I do mean suddenly) picked up to 25 gusting to 30 knots, which was a bit much for me. Again, the boat did well, and I was thankful I didn't have to go forward to drop sails. We motored the rest of the way in.The boat will comfortably eat/sleep 4 adults(pack lightly; storage is at a minimum) or maybe 2 adults/3 small kids.This is my first boat, and I can see it will be a joy to own and sail. Go for it, and good luck!