What a good idea. Alas the pick up pipe position may pose a further difficulty, and repairing damage here turns a 10 minute job into a major headache. Belt strap around the flywheel?
With the spring and cush removed, the nut could be tightened to the required torque, holding the drive sleeve in a way to avoid damage. Marking the nut and crank would enable assembly, tightening 'til the marks line up plus maybe a bit extra for luck, assuming that the drive sleeve and nut can be viewed through the compressed spring and we are not a whole turn too slack.
All fine and dandy, but the problem still remains of holding the crank with the cush assembled. Time served hooligan method was bike in gear, rear brake on and smacking the wrench, peg spanner, C spanner, drift or whatever 'til it felt right. Bearing in mind my earlier comment that some of the torque has to overcome the spring, this alternative method stands a good chance of really loading the sleeve and producing a good clamping force on the bearing against the crank. All a bit long winded for something so simple.
Take your choice, certainly easier to assemble the cush with barrels off, holding the crank still with a wooden block against the crankcase. Rattle gun has my vote.....
Swarfy.