First the good news, I think I have everything working again. So my question has more to do with wanting to know if this is how it should have gone. Also, I don’t think my module admin page is working properly, but there are no errors, just no way to expand the information on the module to upgrade/enable/etc.
The first thing I tried was to do an in place upgrade. I did a snapshot of my VM and then let it rip. After several hours of searching for solutions to one issue after another I ended up punting.
Everything I read said I’d be better off doing a full backup and restoring it to a fresh install. So that’s what I ended up doing this morning. The install was easy enough, the backup was trickier since 13 was so old, I could not easily ssh to/from the machine (ya, I know I put it off way too long).
Doing the restore from the command line seemed to go OK, though a bunch of things that flew by the screen made me wonder how well it would restore everything. The answer seems to be the main stuff did OK, but all of my customization were lost. That included entries in the astdb (though they were on the backup) and a file I added to /etc/asterisk and an override file didn’t make it out the other end. Also, some custom sounds.
The biggest loss, and one I think I’m going to have to live without is all my call accounting records are gone. Going to the cdr report shows no history at all. This seems like it could be an issue for some and I was quite surprised they all went away.