I'm sure anything can be rigged up, like you say, brake switch not working right, etc. Obviously someons been in there messing stuff up, so who knows? The system is exceedingly simple on the earlier trucks ('82 up to who knows when, at latest '87) and doesn't require much at all in the way of wiring and components. I'd verify that first there is voltage getting to the plug at the tranny.
I'm not going to go back through all of the other posts, but you need Vacuum, VSS, and probbaly temp input to lock the transmission up (as well as the brake not being depressed) when the system is working correctly. Cruise is tied into the VSS, so there exists the possibility the VSS has been hacked up, or that the cruise/VSS box (I'm thinking thats what your truck uses to lockup too) has been tampered with. But if you aren't getting voltage when you should be, theres your first problem to solve.