Mind you, I used Gentoo for many years before ubuntu, so I'm used to rolling breakage. Sid is a lot more stable than Gentoo (circa 2010)
Kernel modules are the main things that deteriorate, mostly the GPU support. It's normally a matter of changing the kernel version (I freeze the kernel every time I remember about it) or removing some old package that isn't permitting a clean upgrade.
Last time I reinstalled a desktop was in 2007 (I had 3, now I only have 2), because a Windows machine got a virus at the same LAN, and I wanted to be sure it didn't get anywhere. Last time I reinstalled a laptop was during the setup of my new one, this year, because I got a pretty messed-up set of kernel packages, and decided it were easier to just start from scratch.
Ubuntu solemnly annoyed me by botching every upgrade and forcing me to reinstall every half-year. It was window-esque...