Here is what I ended up with:
1/2 x 7/16 3425 Dual marked Proto Plvmb Marked USA
11/16 open/box 11/16 marked usa traded for a Vlcheck
5469 1/2" speeder with swivel on the bottom marked USA
36** 5/16 obstruction screw driver marked USA
5564 3/4" Drive 2" socket.
8" adjustable wrench. marked USA.
Nothing really early, but it is there.
He has at least 1 complete set of 3 different styles of PLVMB combination wrenches.
Then, I ran out of money after a Wright 3/8 speeder and an old Athol vise. (worthy of it's own post)
There was lots more left of the 3/4" drive. 8 or so sockets, a breaker bar and a sliding T bar.
I spent almost 8 hours looking at tools with this gentleman. His eyesight is going and he can't see well enough to sort wrenches, so that is what we did.
82 years old and still very sharp. Remembers the different manufactures, who they merged with etc. Still has his original PLVMB set he bought when he started working on tractors.