I would start with a talk to the owner and get an impression. Impressions can be misleading
How long have they owned it, what condition was it in when they got it etc.
Pretty much anything has had a repaint, and paint can cover anything, especially recent paint. A good looking 20+ year old paint job is probably covering good quality repairs, if there are any.
If the car is more than 2 or 3 hours away, I have been known to hire an appraiser to look at it. I have also asked an owner to take it into a GM dealership for inspection. Two different approaches.
I figure if I am driving far enough that it is an overnight or longer trip, even if the car is not up to what I understood it was, I am probably going to buy it and bring it home.
You can't expect a "good deal" when you are buying remotely. You just pay the going price! If it was a good deal a local would already own it.
'66 is a nice year, I hope it is a solid car and makes you happy.