Check the shifter linkage very carefully. If it's anything like the ag tractors, moving the shifter from forward sector to reverse sector moves a linkage or cable to shift a valve. If the cable is broken or the shifter worn from going between forward and reverse many times over the life of the tractor, you may not get it to go in reverse.
If that all appears satisfactory, then a set of pressure gauges is usually the best way to diagnose a powershift. You could also start by changing and cutting open transmission filters to check for debris from clutch packs etc.
D2-5J's, D6-9U's, D318 and D333 power units, 12E-99E grader, 922B & 944A wheel loaders, D330C generator set, DW20 water tanker and a bunch of Jersey cows to take care of in my spare time😄