As you already have a boat, you know more about them than me. But I'll tell ya about mine. We got our 1982 34' O'day last august. First sailboat. First boat. We paid to have a marine surveyor check it out. The boat was very well kept by the PO. The only big problem was some soft core starboard of the mast. Haven't fixed it yet. Also very small soft spots here and there near the bow, but otherwise very solid for a 27 year old boat. This past winter we did some work. The ball valves were tight so I greased them. My water intake to the engine was a gate valve so I replaced it.
You probally know all about where water can leak in a boat and other normal boat problems, but I would check:
Stantions. Two have small cracks at the base. Surveyor pointed them out.
Look for gate valves. My water intake for the engine had one.
The keel is cast iron. Check for signs of rust. Mine is excellent and even the keel bolts in the bildge were shiny. Mine is shoal draft.
The surveyor did not crawl behind the engine but last winter I did and had to replace the steering cables. Just one meat hook but I replaced it anyways. (I have wheel stering, factory option I'm told) Also greased the rudder shaft as it has a zerk fitting. Was told ther are two grease fittings but I have only one.
Had mast removed last winter for storage cause I wanted to. The coax to the VHF was fairly new but whoever soldered the PL259 connectors did a very bad job so I repaired them. Installed new mast antenna also.
No hour meter for engine. Engine oil was black so I'll be changing it every month this summer but engine runs fine. PO installed electric fuel pump (replaced engine mounted one), and put a new Rancor fuel filter on.
Sails were in excellent shape but being new to sailing I took the main to a loft to be checked out. Just needed a cleaning. Paid extra to have the O34 insignia put on.
Jib has roller furling. No problems here.
Surveyor checked 120v electrical for proper ground and it was ok
BUT!!!!!
The orange light on the panel to check for polarity from shore power was
DISCONNECTED! Don't know why.
Surveyor said there was an emengercy tiller but we never found one.
Hope this helps. Please ask questions if ya have any.
mitch