1) Boat was serviced only every two years; from comments in the maintenance records I can tell the boat wasn't used very frequently. There was a carb. rebuild and that needed to be redone because of lack of use.
I am not sure if that is a big deal. As long as nothing is broken right now. You may want to pull the drive and see if everything is OK back there
2) I was set to trial the boat and while the marina was cleaning it up, they found that the ujoint bellows was severed. The owner repaired this, and the gimbal bearing was ok; they replaced all three bellows while they were in there.
3) Hull has two dime sized gouges in the fiberglass towards the front of the keel, where it begins to curve upwards; looks like beaching damage. There's also discoloration for about 1-2 feet by 6 in. along one side of the hull below the waterline, towards the front of the boat and near the keel; doesn't look yellowed, but 'whiter' and not as consistent color wise than the rest of the hull.
I would say that is normal. Some times things float right below the water and you hit them with no way to know that there was somthing there. As long as it was sealed and no water got in I would not worry too much about it. As for non consistant color is it staining or somethign else?
4) Skeg is chewed up, but still resembles its original shape- edge looks like ripping a piece of paper in half
par for the course, skegs are meant to be sacrificed, they break all of the time.
5) Outside condition of above-waterline fiberglass is pretty bad; dings, scratches, gouges and self-repairs; about 15 in total. Decals are bad. The vinyl has several punctures and one of the speakers doesn't work.
These are things that happen over time. I would be wondering why they were not addressed though.
6) While I was 'told' that the boat was winterized regularly, I only see one record that shows a 'de-winterization'
As long as the block is not cracked you are fine. Do you have any record or gear lube and oil changes? Winter layup is when most people do those things. I would check how often they were done. If it was only every other year that would be a red flag to me
Based on the items I describe, should I run from this boat?
Depends, its end of season so there will be lots of boats out there for sale. I would look around a bit more and see if there was anything better in my price range.
Am I being too picky?
What else should I look at?
soft spots on the deck, strinniger/transom rot are big things
Thanks!