I have Ubuntu running on three systems at home and as my primary platform at work. I am generally happy with it... except when it comes to upgrading. It seems incapable of managing even simple customizations. The lowest hanging fruit that needs to be plucked is network configuration. At both work and home I am using static IPs. The network management wizard (or whatever it's called) keeps trying to overwrite the interfaces file; I eventually remember how to suppress this via google but it's usually an hour wasted. Worse, during transition to a new version, Ubuntu thoughtfully notes that a variety of configuration files have changed (eg gtetris or some such) proffers a diff, and asks if I want to keep the old one or use a new one. Then it merrily runs off and overwrites all the network configuration information without so much as a how-do-you-do. I was upgrading from 9.04 to 10.04* this morning, and had to recover nameserver and gateway info from a colleague - all I had was loopback setup.
Video and audio always seems to be an issue, too. I had to do a fresh install at home because the system couldn't cope with a change from Nvidia to ATI video chipset, and stopped running anything with OpenGL. Tomorrow I'm wiping the work system with a fresh 10.10 because the Nvidia drivers (pick one of several) are now not being recognized, and even if I get X up with generic drivers the mouse and keyboard are no longer functional in an X session (such that I can't even get out to a shell with Ctrl-Alt-F1), even though the KB is fine prior to X. The last time I ran through an upgrade I had been able to get twinview working after spending a profanity filled day, but audio was somehow collateral damage, even though I didn't muck with anything obviously related to it. I could spend another day pasting bits of my logs into google but would rather spend half a day installing cleanly and restoring my home directory. Ironically I was feeling smug about my Linux platforms having just done this a month ago as a matter of routine Windows maintenance.
* My plan was to stick with 9.04 but I really need Thunderbird 3 to use a javascript filter plugin to compensate for the horror that is our corporate spam "filter", and the non-standard TB3 install suddenly got upset over an updated flash pluggin "shared" (??) with Firefox. I naively thought it would be easier to just bite the bullet and upgrade to a version where TB3 was part of the default install.