The first thing that I check on a truck (or any vehicle) is the brakes!
Aside from simply stepping on the brake pedal and feeling pressure (or not), look under the vehicle, on the inside of the tires. Look for brake fluid leaking out of wheel cylinders and leaving a trail on the inside of the tire. Look at the brake lines (the steel hard lines and the rubber flex lines). Are they wet? If so, there could be a leak.
If the GL rep will let you, open the access door on the floorboard and check the brake fluid level. If it's low, it had to go somewhere...
One thing to check before all this, is the obvious: If the truck has "no brakes" written on the door, windshield, or elsewhere, then there's a good chance that it'll need some work.
All that being said, the brake systems on a Duece or a 5 ton are ridiculously simple, compared to modern ABS systems. Part's are relatively available, and reasonably priced. You don't need any exotic electronic tools to fix them (but a big jack and jackstands are helpful

). The TM's that are on the site are a great reference, and can get you through nearly any repair.
One other thing, if you go and preview and find one you REALLY want, take pictures of it! Document it's condition, so if a GL rep runs a forklift through the radiator, you have some evidence for a claim (or at least a way out without paying a 10% cancellation fee).
Good luck!
Andy