Just about the only initial mis-step in Ubuntu's early structure was deciding to base release on Debian unstable repository. Admittedly, Debian's stable release is notorious for being out of date. But by choosing the unstable release, Ubuntu committed itself to doing the testing carried out by over a thousand Debian developers with only a fraction of their numbers.
This decision explains why Ubuntu has had periodic quality control problems, and, in its early years, was often accused of being slow to fix bugs. Probably the Debian testing repository would have a more reliable basis for Ubuntu.
As things are, Ubuntu has done its best to continue as it began, but not always as well as in its first releases. True, the introduction in the last couple of years of cloud computing, a music store, and a third party repository that includes proprietary software are just as innovative for their time as anything in Warty Warthog.
However, you might question whether these innovations improve the user experience, or have more to do with Canonical's efforts to become profitable. Certainly, no other leading distribution has apparently felt the need for such features yet -- but the verdict may be still out.
Similarly, Ubuntu has had an uneasy relationship with proprietary drivers for video and wireless cards – they’ve included them, yet until recently not made them easy to find. Unlike Fedora, which has taken a firm position against including proprietary drivers, Ubuntu has seemed unsure whether to include them and improve the user experience, or to take a principled stand against them. At various times, it has been seen as doing both.
But undoubtedly the most ambiguous of Ubuntu's moves has been to take the concern with usability to an extreme. No one can argue with the small improvements of Ubuntu's early years. Nor could anyone, in theory, object to Shuttleworth's call in 2008 to make the free desktop rival Apple's for efficiency and visual appeal.
Yet, at the same time, no one could have foreseen that this call for greater usability would have resulted in Ubuntu spending months choosing a new default color palette or taking a year and a half designing the Unity desktop. Given Ubuntu's limited resources compared to GNOME or KDE, you have to wonder whether they were worthwhile -- particularly in retrospect, since the user response has been so mixed.
Even more importantly, these priorities have isolated Ubuntu from the larger free and open source community. While in 2006, Shuttleworth was calling on major projects to coordinate their release cycles, Ubuntu has moved to developing its key pieces of software mostly in-house.
That this arrangement creates labor shortages is suggested by the recent call for developers to work on Ubuntu projects -- a call that, considering Ubuntu's insistence on copyright assignment, seems unlikely to be greeted with much enthusiasm.
Acquaintances within Ubuntu deny my intepretation, but it looks very much to me as though Ubuntu in general and Shuttleworth in particular attempted to assume the leadership of free software development and became impatient when they didn't immediately get the results they wanted.
When the attempt proved slow and difficult, they withdrew. This position reduced the problem of cooperation with other projects, but at the expense of becoming more self-reliant.
In effect, Ubuntu has become the China of free software. Too large to ignore, it paradoxically remains both isolated and influential. The result is probably Ubuntu's second greatest failure to date.
The greatest failure? That would have to be the failure to develop a smooth relationship between Ubuntu and Canonical.
Unlike openSUSE and Fedora, Ubuntu has never truly become independent of its commercial sponsor. Like other distributions linked to businesses, Ubuntu has benefited from both labor and resources donated from its corporate sponsor. But the difference is that Ubuntu has never been self-governing in the sense that openSUSE and Fedora are.
When Mark Shuttleworth decides on a new direction for Ubuntu, the community has few choices except to go along with it. Individuals can question the new direction on mailing lists or by leaving comments on Shuttleworth blog, but no one has any authority to override or modify it.