Andy you should watch this video and it will give you an idea of what is happening inside your 5-speed shifting issues. https://www.youtube.com/watch?v=6UnFDaAdBaM
I have done this repair on a few 5-speeds and it makes a night and day difference drive

Gus beer

64 Plymouth Savoy
493 Indy EZ's by Nick at Compu-Flow
5-Speed Richmond faceplate Liberty box
Dana 60