I can't help much, but hate to see questions go unanswered, so will give you what I have, and maybe it will provoke other replies. I raced against an older Hunter 27 for a few years, and, in the hands of a skilled sailor, it sailed very well. The owner never mentioned any behavioral quirks about the boat, so I think it would be as good a learning platform, and as easy to sail, as any 27' cruising boat of similar design.
An excellent resource for self-evaluating an older boat is Don Casey's book, "Inspecting the Aging Sailboat". There are also marine surveyors who will inspect used boats for a fee and provide a report, listing defects that they found.
There are so many things that should be examined on a sailboat that I'm hesitant to try listing them all, but the Casey book is comprehensive. I will mention, however, that you should examine the standing rigging and the chainplates, because they hold up the mast, and can be expensive to replace. You should inspect the through-hulls, because, on some older, smaller boats, gate valves were used instead of proper through hull valves. Also, if they aren't adequately caulked, they can leak and cause severe damage to the hull if it's balsa cored, and old gate valves have occasionally been known to suffer sudden failure, resulting in a sinking. Look for excess play in the rudder, and look for signs of old damage, such as cracks around the keel stub, indicating a hard grounding. Inside, look for water stains that provide evidence of long term leaks, that might have caused damage as a result of being ignored.
The age of a boat is no determiner of its seaworthiness. There are great old boats still sailing if they have been well maintained and repaired. Good luck!