Doing deals with OEMs actually seems like a better strategy today than it was even just a few years ago when Canonical did their original deal with Dell.
For one thing, Ubuntu has (for better or worse) made significant progress toward their UI vision. Unity has been polarizing, but many users (especially the "normal" people who are likely to buy an Inspiron or similar) seem to like it.
Even more importantly, a significant number of users today (in any case, more than there were back then) basically only care about having a web browser installed. This means they are less likely to care about having MS Windows (FF and Chrome run on all three "major" platforms).
I only using a web browser and emacs and don't care about polish much. 1) Canonical did a good thing by owning the UI with Unity; they should make it cooler, more beautiful with every release 2) They should focus on providing several high end, many low end models for developers, and experiment better with ARM based models, for example raspberry pi ubuntu 3) 6 months intervals seem to frequent now and maybe it would be better to shift to yearly releases. 4) the software center should be improved better and better.
But when Microsoft change the GUI (as they did between 3.1 and 95, 2000 and XP, XP and Vista and will between Vista and Windows 8) so there is always going to be relearning as technology advances.
Shouldn't people have the choice which new GUI they learn?
And the relearning curve doesn't seem to be hindering the Mac, or the iPad, both of which face the same challenge and yet are taking market share.
Also, I think this is slowly becoming less of an issue. A substantial number (10-15% of global PC market share, depending who you ask) of users have made the jump to Mac, which is quite different from Windows. And on top of that, many now use iPads or Android tablets, with even newer UI paradigms.
When you combine this with much of your data now being available through cloud services, the barrier for trying something like Linux should become lower.
For one thing, Ubuntu has (for better or worse) made significant progress toward their UI vision. Unity has been polarizing, but many users (especially the "normal" people who are likely to buy an Inspiron or similar) seem to like it.
Even more importantly, a significant number of users today (in any case, more than there were back then) basically only care about having a web browser installed. This means they are less likely to care about having MS Windows (FF and Chrome run on all three "major" platforms).