I'll be curious to see how Ubuntu handles it. It's definitely an inherent problem in a rolling release distro, but it's far from insurmountable. Of all distro's, I'd expect Ubuntu to try and tackle it since it'll the first(?) non-power user distro to try a rolling release model.
Example:
Keep configuration file conversion information separate from the versioned packages. Then if a user tries upgrading package foo-10 to foo-14, but there was a configuration file conversion between foo<=12 and foo>=13, the package manager knows to still do it.
Ubuntu discussing moving to LTS + rolling release model
Posted Mar 2, 2013 10:15 UTC (Sat) by jospoortvliet (subscriber, #33164)
[Link]
http://opensuse.org/tumbleweed would be the first. But it isn't exactly what Ubuntu proposes or what debian has - it is more a have-your-cake-and-eat-it-too solution and not as truly rolling as say Gentoo is.