Assumptions:
The 2-3 shift won't happen until the engine defuels or you lift off the throttle
The OD shift happens but only if you have the accelerator positon and speed and you hold your mouth just so
You have adjusted the TV cable correctly
Conclusion:
You are loosing fluid pressure for the 3rd gear apply and it won't overcome the TV pressure as it should. Most common problem is a worn or torn lip seal on the direct clutch pack. A sticking valve in the VB could also be the culprit.
How firm is the 2-3 shift when it happens? Is there any indication of slipping in drive after the shift happens? Slipping or mushy feel in OD?
Response:
Your conclusions are absolutely right! I am not sure how to correctly adjust the TV cable (I assunme this is the cable that works off the injection pump linkage, parallel to the throttle cable). I did have to replace the return spring for it recently, but took it up the road to test and it was still doing the same thing.
The 2-3 shift is sloppy when it does happen, but I thought that was because it won't occur when throttle is applied, so it just kind of "flutters" into 3rd. Once it is in, you can mash down on the throttle and it pulls great. Sometimes the shift into O/D is finicky, like you described, but it also pulls well in it once engaged. There does not seem to be any slippage.
Breaking (BAD) news!
Today, the mechanic that drives this truck started it up and warmed it a few minutes like I told him to do (in neutral) and went to take off and it will not move at all now in either direction...
I hate to do a total rebuild because this thing was just pulling so well, but if it has to come out, it is getting rebuilt and beefed up!
It has 140,000ish miles and is bone stock with an open service body and single rear wheels. Any final suggestions?