I've been an erstwhile FreeBSD user since v2.x (ca. December 1996), running FreeBSD on my own machines since v4.x (ca 2001), and started using it as my primary

I've been an erstwhile FreeBSD user since v2.x (ca. December 1996), running FreeBSD on my own machines since v4.x (ca 2001), and started using it as my primary laptop/desktop daily driver since v5.3 (ca. November 2004). Prior to that, SunOS/Solaris was my drug of choice. In the past, I would update the OS and ports religiously, sometimes rebuilding world and packages on a weekly basis. I've never once experienced any bumpiness between v5.x and v8.x (or any other version, but see my comments on v13 below). The OS has always been rock solid. I have occasionally experienced some package issues, usually when upgrading a port that had lagging dependencies -- some packages written in PHP come readily to mind. The number of times this has happened is more than 2 and less than 6, and in each of those cases, using portdowngrade and waiting it out a few weeks did the trick. Apart from OS-independent hardware issues, the only real FreeBSD issue that I've ever encountered was in the v12->v13 upgrade. If you were running ZFS, there was a gpart bootcode command you needed to run as part of the upgrade process, which I sometimes forgot to do, which caused the post-upgrade reboot to hang. Normally this wouldn't be a big deal, you just insert the rescue CD and run the command and be on your way 2 minutes later; but at that time I had a number of my servers running on a VPS provider that didn't allow you to mount your own ISO, so I had to wipe the machine and reinstall the OS from scratch and restore stuff from backups. I don't really count this as a FreeBSD issue per se, just an obtuse service provider. (I've since moved most of my digital properties oceans away from that company.) Nowadays I upgrade the OS and packages far less frequently. I upgrade the OS with every minor release and also if there are any security issues that affect me. I upgrade the packages every couple of months, or if there is a bugfix that affects me, or if I need a new feature only available in a newer release. Since I started using it, there have been a number of developments that have made my FreeBSD life so much better: cperciva's portsnap and freebsd-update, pkg-ng, and of course the biggest one: ZFS. All of these allow me to maintain and upgrade the systems very easily. I stick with FreeBSD because of its consistency and ease of use, so I'd be curious to know what you mean by "bumpy"?