I've read some interesting things on hunters online, seems there are quite a bit of people that think they are poorly made boats, but then again some that swear by them. Hmm. Also, I need to ask more questions, wonder what some really helpful ones would be, over the phone, before I make the drive, if I do. This does appear though to not be too bad of a deal, but no motor.
Hunters are what they are - not for crossing the Atlantic. Any similar trailerable is going to be lightly built. You wouldn't want to spend forever attaching triple stays etc etc, you want to get the mast up quick and get out there.
Instead of questions, ask the seller to send pictures showing chainplates inside and outside, bilge, rudder post, centerboard pin & winch, etc etc. You can ask him if there are any soft spots on the deck or cabin top.