We've had a 1992 33.5 for about 2 years now and we love her. She sails well, is roomy, and not too hard work on. Access leaves a bit to be desired given the hull insert but its not too bad. Few things I would look out for if I was to go looking for another:
-Leaks in the salon windows on the starboard side result in water running to the wood bulkheads and flooring in the aft berth. Look closely for rot.
-Check drainage on the mast - your boat should have a aluminum mast support. Water tends to follow the wiring down from the top of the mast and make its way into the shower drain. This was a problem on older boats with the wood supports.
-If you have any leaks in the companionway door, the water will drain directly on top of the engine. Look for excessive corrosion on the top surfaces. My engine has really good compression but the injector directly under the companion way was shot and a PITA to get out because water had made its way between the injector and the head (rusting it in place).
-The pressure relief valve on the water heater will result in excessive moisture on the wood footing of the sink area. Look for rot or mold.
-Water tank is aluminum with poor access and no cleanout. Look for corrosion.
-Fuel tank is aluminum and mounted under the batteries with poor access.
-Fuel filter is undersized. I replaced it with a larger Racor unit.
-There is no cut off valve at the tank side of the filter. Suggest added one.
-Batteries on my boat were a mess as was the switch and shore power correction. Lots of corrosion. I ended up having to completely rewire the distribution panel. Good news is that you can mount common bus bars on the back bulkhead and there is plenty of space for a newer panel/shore power connector. Was a fun/educational weekend project.
-The drum for the headsail furler is mounted at deck level. It tends to rub against the opening it sits in. Adjusting tension on the rigging will help a bit but its tough to get it to move freely - terrible design.
-My boat is bone dry now, but spent a lot of time looking for leaks in the first few months. End up rebedding 3 of the four salon windows and building a custom cover for the instruments mounted in the helm area to get her dry. Only time you should see water in the boat is when a bit comes though the mast stepping - haven't figured out how to stop that yet...
-Biggest issue was the keel which was badly corroded. Ended up having a yard sand it down and encapsulate it. Also tightened the keel bolts. Had a small amount of seepage for a week after and now the bolts are dry with no visible corrosion on the keel. Pay close attention to both the keel bolts (corrosion) and the keel. Its cast iron so you're likely going to have to encapsulate if at some point if it hasn't been already.
To the question about your deck. My surveyor spend quite a bit of time with his hammer checking it out. I followed along the whole way - its a fairly reliable way to know if the deck is in good shape.
Anyway, I'm certainly not the most experienced person here, but I've enjoyed working on and sailing the boat immensely. Hope some of this helps.
Thx,
Calvin