Depends on where the valve is stuck in the governor housing I think. It's been a long time since I have worked on one too. LOL
And if the gear is stripped, you're right, it won't shift at all.
But he should be able to tell whether he is starting out in first or second.
He can start off at a low speed with it in drive or second and see how the engine acts, then do the same thing by manually putting it in low he can see if it's a bit easier for the engine to start the vehicle off.
He could also take off in drive or second and get about 5 - 10mph and manually down shift to low. If it down shifts manually into low then he would be starting off in second. He would be able to tell this because it would act like he hit the brakes.
My bet is the govenor has some trash stuck in the bore.