Originally Posted by Brucerobs2
I own a 1980 H27 and Have had it for 5 years, and it's been a great boat. I sail on the Chesapeake, and use the boat regularly for day sails, overnights, and occasionally race it on Wednesday nights. The Cherubini designed Hunters are solid boats, sail as well as their peers (Catalina, ODay, Ericson, etc). Based on your intended usage, and that it's your first boat, it would serve you well. It is not a blue water cruiser, nor is it racy, but a good all around classic plastic, coastal cruiser.
As you look at boats in this price range and vintage, I think condition becomes possibly the most important variable. I'd buy an older, well maintained boat, over a newer, neglected one any day. In general, boats don't hold up well to neglect. Its a 30 yr old boat, there will be issues with it. Unless you want to spend your free time rebuilding a boat, find one that has been well maintained, upgraded, and used regularly. You will find Hunter, Catalina, Ericson, Beneteau's from that era all reasonably similar. What sets them apart is how well they are maintained.
Get it surveyed unless you are willing to gamble on a large repair bill later (yes its expensive but can save you money down the road), make sure the major/expensive things are sound (hull, deck, rigging, motor). The Yanmar Diesel mentioned is much better than the Renault motor that many came with.
The H27 would be worthy of consideration if it checks out on inspection. I have also sailed, and owned a Catalina 27 and found it very similar in its sailing manners, speed, feel, and build. They are both decent boats, very common, and have a good resale market when you are ready to get a bigger one.