SW will need to close and then crashes after closing a model or drawing at random. Sometimes with 5 files open. Sometimes with 10 files open. Sometimes with 1 file open. This also happens on one other coworker's machine. Produces a crash report and successfully sends crash report 9 times out of 10. I am leaning towards it being a PDM issue.

Secondly,

If you upgrade to a new SP for SW, do you need to upgrade the PDM to the same SP? For example going from SW 2019 SP3, PDM SP3 to SW 2019 SP5 but leaving PDM on SP3.