I disagree with the "older trucks are a big hassle" statement. Older trucks, like the M35A2 are bulletproof if you maintain them properly. That being said, beat it hard and you should expect to put some $$ into fixing the stuff you break. These trucks have been around for years and were designed to be serviced/serviceable in isolated areas/regions. No complicated electronics, no CTIS stuff, no automatic trannys, just a truck designed to do its job under very harsh conditions.
I don't agree with the statement that "older trucks are a big hassle" either. They are high maintenance though. Just like "DeadParrot" mentioned in his post. All parts should be considered "at end of life" , especially after 40 to 50 years of service. I was extremely lucky to find and buy a 1988 Deuce with under 50,000 miles of documented use, but even so there were many parts that needed replacing. The rubber parts alone after 30 years have all started to deteriorate. That as one of the first major projects I tackled. Almost all the wiring was rotting away (at least the connectors where) . Replaced everything from under the dash to the front end and back end. Totally rebuilt the cab. The list just goes on and on. Does that mean the truck is a "hassle" ? No, I knew what I was getting into. Any older vehicle would have the same problems.
The whole original question from the "OP" was buying and using a truck that was "trouble free" for at least 10,000 miles.
That basically eliminates "any" vehicle on the road that is over 20 years old. I could go out and buy a 2008 Chevy truck and after only 50 miles have the transmission go out, or something else major. Unless you "Know" for a fact that the transmission has been rebuilt or maintained properly you cannot depend on it. That goes for every major part on that truck.
Are deuces more trouble then the average truck ? Yes they are. Just by their very nature they shack more causing loose bolts. They cause more driveline "stress" then a normal truck. They "leak" more causing other problems like rust and corrosion to wiring. The suspension design causes severe wear to bushings. The list goes on. The fact is though we all "LOVE" our deuces and take them with all their faults. Now does this type of vehicle lend itself to someone who is looking for a "trouble free" vehicle ? Lets be honest, the answer is no.