The Bendix can get gummy so that the gear doesn't retract as smoothly as it should, but I now suspect that there's more wrong with it than that.
The gear is on a steep spiral. When the starter motor kicks off, the inertia of the gear kicks it out, against a spring, and into the teeth on the flywheel. Once it gets that far the torque of the starter motor pulls it all the way up the spiral into full engagement.
When the engine starts it runs faster than the starter motor. That drives the gear back down the spiral out of engagement, and the spring holds it there.
For it to stay engaged after the engine starts, the gear has to very strongly resist following the spiral, sliding in and out on the shaft. The good thing is that the Bendix is cheap, and easy to replace. About $20 and an hour of work is all it takes.
It's good to carry a spare Bendix, since engaging the starter into a running engine can break it in an instant. I suggest that you pick one up. Then pull the starter and see if the gear works smoothly, and about the same as the new one. If it doesn't, and cleaning and a few drops of oil don't correct it, put the new one on.
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