Jayce
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I do upgrades with the distant expectation that I may have issues. I have never had issues with upgrading Ubuntu, but I've read about issues on the forums. Likewise, upgrading in general is kind of a bad idea in my opinion. Just take a look at Windows in terms of upgrading from one version to another. I just don't think it makes the most sense as an operating system to "upgrade". I think the solidified "versions" are much more reliable. I would put much more trust into Vista as opposed to an XP ---> Vista upgrade, for example. Just my opinion, though.
Seems the most sensible way to me (probably why I use it!), you upgrade whichever piece of software you want to whenever a new version of it comes out, including the kernel. Since an OS isn't really a piece of software itself but rather a set of individual programs.
