If you have the space and time it shouldnt be any problem. Go get the Haynes Manual for the truck. You will have to remove the shifter, the exhaust Y pipe (depending on the rust level, fairly easy to do when you take the cat with it) both driveshafts (not too bad, again depends on the rust) transfer case (awkward but possible) and the tranny out ( 90% of my swearing when I replaced my tranny) The only thing close to a "special" tool I suggest is a flex head socket wrench ($20 at Home Depot) and a piece of 1" pipe (for leverage at times) I would think that doing the clutch might be a bit easier than the tranny though, you might not have to drop them to the floor, just slide it back. I didnt have a tranny jack, I just carefully balanced things. For putting the tranny back in I put a steel pipe over the tranny tunnel hump inside the truck and used a ratchet strap to help lift it.
I dont look for help. With you and your son working at it this should be a good project for you both. If it were my kids truck I would play supervisor except for the heavy stuff. Good luck to both of you. PM me if you want a better rundown before buying the manual
96 STX 4x4 Extra Cab
4.whoa 5-speed (rebuilt unit by Kormex Transmission - EBay seller A+ from me)
Rancho RS5000 Shocks
Bridgestone Dueler 31 x 10.5
Lakeland colormatched cap[COLOR]
Silence is Golden...Duct Tape is Silver