I was in a similar situation: here is a reference “guide” that I wrote up. Summarizing some lessons learned. I didn’t go 2.319 to current, but I did make some leaps and bounds. Read thru, and follow up with questions. For note, I am on RHEL8 as well.
Issues include: not upgrading using the same path as install; there is a key change in when accessing the repos, you will need to care for; backups will save your butt.
I recommend a sandbox server/VM if you can, and rollback procedures.