Hi Worty
The shaft keyway looks fairly buggered
This will have raised the metal fractionally on either side of the slot
You have not shown us what th inside of the shaft adaptor looks like? Is it as bad?
So, file either side of the shaft keyway a touch to get rid of any high spots the same with the adaptor
Them lap the adaptor to the shaft, just a touch at first, look for any high spots, file these down and repeat
If you get maybe 75% contact I would be happy enough
Attempt to make a stepped key that is as tight as possible in the shaft and adaptor, measure the adaptor keyway slot and make the top half of the key a little less than this so it has a better chance of staying straight, too high and the adaptor will not seat on the shaft
It might take a few attempts to get the key as good as possible
Alternatively, If you can get the taper to 75% or so contact I would use Loctite 648 retainer grade without any key
and tighten the nut to fully FT
It is also possible to change the gearbox mainshaft without a complete gearbox strip, It takes a bit of care but it is possible
The clutch chainwheel is not running in line with the crank sprocket or has been in the past
I posted a thread about this some time ago,,
https://www.a7a10.net/forum/index.php?topic=9646.msg70166#msg70166John