Your bolt assembly is same as mine. My sear is square cut with no roundness at all(edges just cleaned to not be sharp).Could be the culprit for not re cocking.
Check to make sure the shell cut off bracket(u shaped piece on the mag tube) is functioning properly or the shells will hang up(if dirty) or sometimes feed too fast( if spring is broke/weak). Try moving the action slowly while watching the face of the bolt while shells are feeding. I would bet the shells aren't getting under the extractor during loading(from the picture with the shell in it). I have had more 22's with this issue than any other over the years. Alignment(as mentioned) is also a good possibility.
Very nice pictures. They show great details!
Scott....
I guess my question would be is it okay to try and square the edges on the sear back again or would that change the tolerances too much?
The cartridge cut off assembly is clean, and damage free as best as I can determine. I lubricated lightly with graphite lube. The mag tubes have been cleaned and lubed, inside tube and outside tube. After reading comments from Mossberg they recommended against removing the mag tube and cut off bracket because alignment is critical so I have not removed them, just cleaned and lubed. That doesn't mean that the previous owner didn't take them apart. I have watched carefully as the bolt closed and opened over the mag feed assembly and they look good to me....keeping in mind that I am not a gunsmith.
After today at this point I am considering replacing the sear/trigger/safety group if parts are available.

