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Weird. Its since 8.04 and onwards that upgrades STOPPED breaking things for me. Its been a golden era for Ubuntu.

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.

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