My nickle's worth and I'm no expert. No advice but just my thoughts. If he has 40 grand in it 5 years ago he paid top hourly rate and top prices and had every bit of the work done by someone else. If he drove it in and said "fix it" I do not doubt the 40K. However, I personally would not pay even half that(20K) unless I wanted it REAL bad and had DEEP pockets.
There are some nice trucks out there, upgraded for safety, for a lot less money.
I have a friend who purchased a fully restored 40's model for 16K and its a beauty.
Unless you want THAT truck I'd see what I could buy for the same money...or less money.
I'm sure others have differing opinions but that is mine.
Another question is these current pictures or some he took from 5 years ago? Pictures can hide a thousand sins.
Hope I haven't offended anyone.