My 28.5
First I heartily agree that if the boat still has gate valves they must be yanked and replaced. Risk of catastrophic failure is very high. You may be required to replace them by the marine insurance company. I was required to remove them, and no regrets there because I discovered all but one were totally shot. Second, I also agree rudder blisters and delamination are both common and aggrevating. But repairs are an ounce of prevention for the pound of cure replacing the thing. I have cured nearly 20 blisters and one 8" diameter delaminated area. The rudder is currently baking under (low) heat lamps. Also take note that you are not supposed to paint the rudder with a dark bottom paint. OEM says this causes overheating and leads to delamination. Third, the stuffing box drip does drain into the area that is designed to trap oil and/or spilt fuel from the engine and keep it out of the bilge, which is a very good thing. Take note that there are weep holes on either side of the engine mount fiberglass at the base of the engine compartment. However, I believe water will flow over the stringer in front of the engine compartment and beneath the floor before it would back up high enough to make it to these two weep holes.Fourth, never had a problem with the rig though I can see where sail chaffe can be a problem. So far so good for me. We gybe downwind. I think it a more fun anyway.Fifth, the plastic stuffing box is not a problem. I replaced mine when I had to replace a bent propeller shaft. But the plastic nut seemed in good shape after 15 years of service. It was a 'might as well' afterthought during the shaft replacement. I went with a traditional bronze stuffing box w/drip as I felt the dripless box was too expensive for the supposed benefit.In my biased opinion, the 28.5 is one of the best day-sailor's on the used boat market. Fun to sail, and enough amenities to accomodate over-night stays.