Since there are some inherent concerns regarding switching Ubuntu to a full-on rolling release, perhaps the best approach is a "partly rolling release" distribution instead.
This would protect the system core from breakage during random updates, while keeping the software fresher than what we're seeing now.
What would this look like on a newbie friendly distribution? I'd point to PCLinuxOS as an example of a distribution that is already doing this successfully. PCLinuxOS offers a partial rolling release that provides users with a ton of great application updates, while protecting the underpinnings of the distro. Because of this, PCLinuxOS prevents the typical newbie from having a bad experience.
I know of PCLinuxOS users who have had the same install running for two years without ever needing to reinstall. Best of all, these users are running a fully updated system. As an Ubuntu user I find this concept interesting and a bit unusual, as a clean install of Ubuntu is sometimes needed due to the nature of the distribution.
The ten thousand dollar question should be, would a rolling release even work considering Ubuntu is trying to target the server, mobile and desktop markets all at once? At this point, all signs point to this being problematic. Still, for desktop users, I believe an Ubuntu rolling release may need to happen eventually.
I hate to admit it, but honestly, going outside of the Ubuntu Software Center to get an up-to-date release of common software is tiresome. In the past, Linux software solutions such as Klik offered a unique way of installing software onto a Linux distro without concern over meeting dependencies. Best of all, it worked in a uniform way for users of any and all distributions.
Today Klik is no more, however PortableLinuxApps is still available for those who wish to experience a single file application installation under Ubuntu.
Despite being flawed on many levels, PortableLinuxApps does shine some light on one approach to providing new software versions regardless of the Linux distribution release. This type of approach has proved to be successful for Unix operating systems such as OS X. Unfortunately, however, the PortableLinuxApps approach does lack the ability to update to the latest software, like we enjoy with APT. Regardless, the idea of a self-contained software "image" for the Ubuntu desktop is fascinating, and I wouldn't completely rule out the possibility that one day this could be part of the Ubuntu experience.
Would it work as a satisfactory alternative to a rolling distribution? It's a possibility. It could prevent users from hosing their core system-wide installation, while still being able to use non-release centric software.
Where Ubuntu will take us with regard to software availability and system stability is still foggy right now. However, one thing is for sure at this point, there are no plans on changing their existing release strategy just yet.