There are a pair of opposing bevel washers that act as a spring between 1st and 5th input gears, that stops 5th from spinning too freely and getting stuck in the way of the dogs on the side of 4th input when trying to engage 5th. If these washers were flattened out then it will become hard to get it into 5th.
Dogs could be rounded too..
The 4th output gear is known to be relatively weak, this why Robinson industries makes a billet one. Yours could be partially busted hence the juddering.
In any case these are examples and untimately guesswork until you split those cases
You will know more by simply dropping the sump first though.