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I don't think you're that far off base ... I usually buy 20-30 year old boats so I have a different perspective.
Sailboat diesels often don't go more than 2000 hours between overhauls. This is NOT because the diesels have a short life, but because it often takes decades to accumulate that many hours. Despite their high revs, these small diesels are NOT highly stressed motors, and if run a lot (at a reasonable load - say 65% - 80%) are likely in better shape than if barely run at all.
Sorry about my goof, assuming that the boat had been run for 2 years, not three. Around here, light use is considered to be 1/2 to 1 day of sailing a week. Generally that adds up to about 1-2 hours a week on the engine. Maybe your area requires a lot more motoring.
If the wind is up, I run the motor about 30-45 minutes total - just to get in and out of the marina and the inner harbor. But, when I was cruising last summer, I had several days when I needed to get somewhere and there was no wind. On those days, I ran the engine 8-10 hours a day. Had I been home, I wouldn't have been out on those days.
As to whether a surveyer will look at sails, if the mast is up and the sails are bent on, they can give you a reasonably educated opinion, which should be enough. BUT, if the sails are bagged, my experience after 3 purchases is that they will pull out a corner and say "I can't really tell you about the whole sail, but the corner of this sail looks new/decent/worn/dead".
This isn't bad, but an in-depth inspection will tell you more. I've experience all of the following: the spreader patch is in the wrong place and the jib is being damaged; the sail has been exposed without its cover and one part of it is rotted; or the sails don't match the inventory. Of course, all of this is less likely on such a new boat.
A sailmaker around here would probably charge around $100 - $200 to give a full set of sails a once-over. You could call one and ask, but given the overall perspective of the cost of the boat, it may not be worth the time and effort. A new main and jib for your boat would be in the ballpark of 4-5 k from a big name sailmaker, and I doubt that the sails are completely worn out after three years in the Chesapeake area, so it's not anywhere as big a deal as the engine.
I don't know of any other specialists, but I would also talk to the owner or techs at the yard that has been servicing the boat. You should ask for the service records if they have them. Obviously, if the owner had done all his or her own maintenance, then this information won't be available.
I do have a couple of other suggestions:
You should absolutely insist on a sea trial. It is good to have the surveyer onboard for the sea trial, if you can get it arranged. It is also good if you can get the owner to come too, as he or she will know how the rigging should be set up and what the quirks are. A couple of hours with the owner can save you a lot of puzzlement later on.
Also, before the survey, I would go over the boat and take notes as to any questions you may have. I would also follow the surveyer around with a notepad and feel free to ask any reasonable questions that come to mind.
It is good to remember that surveyers, mechanics etc. are not omnipotent, and can miss things. You are cutting down on surprises, but cannot completely eliminate them. For example, I had a worn shaft coupler and shaft, due to prior engine mis-alignment, which in turn had been due to a motor mount adjusting nut vibrating loose (not a PSC issue). Neither the mechanic nor the surveyer spotted this, and it was not discovered until I had had the boat for a year.
This repair required a new shaft and coupler (about $500) and since the rudder had to come out to pull the shaft, I combined this repair with replacing the worn out cutlass bearing.