1939 B High/Low Shifter Problem

I have a 39 B that has a hard time going from high range back to low. It will go from low to high no problem but I usually have to let the tractor die and turn the flywheel to get it to finally click back over to low. It's annoying because 1-2 are too slow for what I do with the tractor and reverse is only on the low side. Is there something I should expect to find it when I tear it apart to fix?

The pto is also stuck on and the lever will spin freely so I believe the fork is broken there.
 
The HL (High Low) range gear is the first / closest gear to the input TDS (Transmission Drive Shaft) the bearing in the center of the TDS carries / couples up to the TTS (Top Transmission Shaft). The HL gear gear is either in a direct (High) or under drive (Low) position. If problem shifting occurs when shifting to high, that is when HL gear is trying to couple directly to the TDS. The most likely reason it does not want to join is the bearing inside the TDS is loose / failed. If this bearing was loose enough to not maintain the two (TDS and TS) shaft alignment it will affect the two matching gear from coupling / shifting together.
 
I had a n old tranny giving me fits until I followed the advice of making the shift when the clutch pulley is still rotating just a little bit before it comes to a stop. What can it hurt to try? Good luck!
 
When spinning the lever will just kinda bounce across the teeth but not catch, I dont remember it making any grinding noise though.
 

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