[loeg]

> I've found with Linux distributions that aren't rolling releases, things tend to break in annoying and insidious ways, such that you generally need to, or at least it is strongly advisable to, fresh install each time.

I think this is generally not true, at least of the major distributions. Others have already commented about Debian and Ubuntu, to which I want to add that updating Fedora over many, many releases has been completely seamless for me. The dnf system-upgrade plugin Just Works.