Welp, I took the plunge a couple weeks ago, and all is well.
I followed another thread on here that suggested some pre-activities like backing up the apps directory, VMs, and removing some unsupported plugins. I also ran the upgrade helper and it guided me through most of it. It's worth noting that I have a very straight-forward setup with only a couple docker containers and VMs.
Most importantly, I backed-up the USB so that if anything went wrong, I had an avenue to revert back.