Hi Bill, wear on the pinion and ratchet should make it catch first and then jump out I guess.
If they are worn it could be a costly affair, as you'll need to change the lot (pinion, ratchet and kickstart quadant).
It seems more plausible to me that the pinion gets jammed on the bush, either because it's to tight or to loose.
If there is excessive play on the kickstart shaft/bushes, it may also be that the quadrant pushes the pinion away from the ratchet giving the symptoms you describe.
I suppose you already ruled out the possibility of a slipping clutch?