Hi @MattWynn I'm currently using Vault Basic 2022.0.1 and Inventor Professional 2022.0.1.
I've been using Inventor and Vault together since mid 2018 (meaning since Inventor 2019) and adding source files from Vault in the nesting environment worked from then up until some time last fall I think (maybe earlier). It stopped working some time ago, but I didn't find it bothersome until recently. The nesting environment was actually the main reason we got the PD&M package to begin with.
Regarding updates, I tend to do them as soon as they are available to me through the Autodesk Desktop App. I also do Windows updates regularly, but it doesen't feel like that is to blame in this particular case.