Thanks buddy. Figured if anyone here has seen a failure on an older club car it's you :)
I did forget to mention I did check the input shaft and it has no play at all. It's nice and tight. I'm guessing the shift collar or synchro being worn out. Usually with a car if you have to hold it in gear that's what it is (not that anybody drives a manual anymore but me apparently lol)
I'll probably just buy a new rear and call it a day. I'll repair this when I get some free time and decide what to do with it from there :)
When that time comes I'll update this post with pictures and root cause for future searches.
