I have exactly the same setup but on a '47. Good to see others have found these rare workhorses!
Keep us updated on progress and if your able to get the winch working!
I'm sure the winch won't take much to get working, the previous owner actually used this truck to build his workshop

I bought a 1959 Spartan 10 at auction a couple of years ago. About all I have done with it is haul it down here from Colorado. I bought it mainly because they are rare. It is the only Chevrolet I own. The rest are all GMC.
https://photos.app.goo.gl/CGKaZC1akoywmTAv8The 10 hole Budd wheels are really not that rare, but more Chevrolet trucks were specced with spoke instead of Budd. Budd wheels were the standard on larger trucks, especilly west of the Rockies. Air brakes are much simpler to fix than hydraulic. I have been running trucks with air brakes for over 55 years, and they haven't changed that much.
Man I love the look of that truck! The airhorns look pretty cool on it. Though I think yours is a 1958, judging by the emblems
And thanks for the clarification on the wheels, they're gonna be coming off anyways.