> Then I had enough, whiped the whole thing and in 5 minutes installed the FreeBSD base system. A handful of binary packages and a couple of edits to config files later everything worked perfectly.
There seems to be some confirmation bias here. Is writing an iso, installing an OS, installing a “handful” of packages, and configuring everything not somewhat equivalent to the “messy” alternative of upgrading Ubuntu? I bet they were very close to the same amount of work, but one might have seemed like more, or more daunting, due to your experience and preference for bsd. Just throwing it out there
As for Ubuntu upgrades, apt-get update, apt-get dist-upgrade, and do-release-upgrade have always worked well for me, though I hardly ever do a major version upgrade and opt to do a fresh install after the first minor point release. If you were jumping major versions or a few major versions, of course packages are going to give you a hard time. I imagine a fresh install might have gone as seemingly smooth as the bsd route you took. Anyway, hacking is hacking, keep at it!