Splines may be shot-- I seem to recall that there was a couple year's model's that has splines that wore quickly. Or, OTOH, the non-flywheel clutch carrier assembly has been known to break the rivets that hold it together. Or, OTOH^2, the bike may have 104,500 miles on the clock.
Pull the tranny and give us pics. Gap Season starts in March, so there's time to get on the road again...
PS-- "GapRunr Dual Sport Touring
" Just visited. Nice stuff. Your store?