It seems like since 8.04 they've changed the package naming conventions for LaTeX twice. That's been the biggest pain about upgrading for me, everything else has been a breeze.

I think they inherited that transition from Debian, where it's also been a bit of a pain. Part of the mess is that it wasn't just repackaging/renaming, but a switch of upstream sources too, which weren't exact drop-in replacements for each other--- teTeX hasn't been actively maintained since 2006, so Debian (and most other distros) shipped to TeX Live as their new upstream.

Yeah, I set up disk encryption for all my partitions except for /boot which If I remember from the install (6.06 LTS) wasn't a standard option at the time, upgrading to 8.04 caused me a whole load of grief.

I know I should rebuild it and it'll probably be fine, but if I was going to rebuild I think I'd use Arch instead (just a personal choice).

But the VMs of Ubuntu that I use of newer versions, yeah they're great.