Hi everyone,
Final got to revisit this and took the tractor back to the cub dealer. It ended up being two bolts the plate at the front of the transmission were loose. Felt a little silly have to take it to the dealer and pay labor for that but at least it's fixed.
Part 11 on this diagram:
http://www.partstree.com/parts/?lc=c...&dn=0053200004
Thanks for all the help!