You asked for it, so here goes…my biased opinion:
Our boat: 1989 Pearson 31-2 with wing keel.
Overall: Would buy again.
We probably looked at 50 boats before buying, so we had a pretty good idea of what was available within driving distance (2 hours or so) of Annapolis. We cruise the boat (mostly just the 2 of us) on the Chesapeake Bay and tributaries. The shoal draft (3’ 11”) keel lets us get in almost anywhere. We routinely stay aboard for 3 day weekends, and have comfortably lived aboard as long as a week. We also day sail with friends. 6 adults in the cockpit is probably as many as you’d want to have. All the lines lead to the cockpit, so single handing is relatively easy. We see Pearsons nearly everywhere we cruise, and they always catch our eye.
Hull: Solid fiberglass. No core. No problems.
Deck: fiberglass with balsa core. I had some leaking around 2 of the stanchions. Easily fixed by overdrilling, scraping out the damp core, filling with epoxy, and re-drilling. This is problem is not specific to Pearsons, but to every boat with a cored deck in which the manufacturer did not perform this task. In other words, most boats that you’ll find on the market. Lots of good gouge on how to perform this routine maintenance.
Engine: My engine is the ubiquitous Yanmar 2GM20. Access to the engine is good (1 of my key criteria), routine maintenance is easy, and parts are readily available. The OEM manual you get with the boat is far from helpful, but aftermarket manuals are excellent.
Headroom: I’m 6’2”, and wanted to be able to stand straight up in at least part of the boat. I can easily stand in the galley and cabin. The head and v-berth area start to get tight.
Equipment: All name brand, with spare/repair/replacement parts readily available (Lewmar, Garhauer, Edson, Ritchie, etc.).
Electronics: Dated. Mine were OEM. The Loran and GPS were as big as small suitcases, and departed the boat the first winter I had her. The rest of the electronics worked during the sea trial, but I’ve slowly removed the original electronics except for the depth sounder, which still works fine. A handheld GPS and mast-mounted windex tell me all I need to know about the wind and my boat speed.
Through-hulls: Most are bronze, but there were a couple near the waterline that were plastic. Surveyor recommended replacement, which I did.
Hatches: Bowmar with parts available as needed (plastic knobs, etc.) The lenses were crazed and the sealant around them had failed, resulting in annoying leaks in the v-berth and head. Lens replacement was a simple, satisfying project that gave me a dry boat.
Plumbing: The pipes between the tanks, pump, and faucets is gray plastic that looks like Pex, but is not. I’ve been told that it called “Qest” and that the fittings are not compatible with Pex. That could make for a small project if a fitting fails and the Pex fittings do not fit. So far, I have not had any issues. I replaced the galley faucet recently, and had no problems.
Things to look for: The aluminum rub rail is very thin, and attachment to the deck/hull joint is subject to coming loose if you do much “rubbing”. Trim covers below the rub rails at the deck/hull joint are plastic and brittle after 25 years. Cracks/broken pieces are unsightly, but really only visible when the boat is on the hard and you’re looking up from the ground. I have seen other Pearsons where the owners have replaced the rub rails, and the results look good. Other owners have complained about the in-boom reefing system. The previous owner of my boat had abandoned the in-boom reefing and installed an aftermarket system that runs the reefing lines around blocks on the outside of the boom. It works fine, and all from the cockpit.
No boat will be perfect in all categories. Settle on a few key criteria (mine were engine condition/access, headroom, and wheel steering), pick the best overall candidate that meets your criteria, and get a survey.
Best of luck!