Just bought one, 3 kids
I just bought a 1976 O'Day 27 in July and love it more every time out. The choice of a boat really depends on your needs. We sail Lake Ontario (as I expect you will) and day-sail the boat most of the time. Our cruises will be short (a long weekend to a week) so we won't have to stow a lot of gear. For extended cruising, it will be a little tight for your family and all of your stuff.My sailing experience is limited to a J24, O'Day 25 and my 27. The 27 shares many of the characteristics of the 25. It is well constructed and is very forgiving if you are a novice or a little rusty, as I am. The 27 is much more comfortable than the smaller, lighter boats. Lake Ontario tends to be very choppy and I really appreciate the extra size and weight of the larger boat. I'm sure the same comparison could be made by moving up to a 29' or 30', but the price of a larger vessel was out of the question for us at this time. Given our use of the boat, we think it's pretty close to perfect.We sail out of Pultneyville, about 20 miles east of Rochester. The PYC web page is http://hometown.aol.com/bristol32/index.htmlGood luck!