I don't know about others, but the way I am, I set out to do something, then do it. As of today, the only thing I've managed to achieve with Linux is… mess with Linux. It's sure fun and interesting, and I learned a bunch of things. The issue is, anything other goal that's not strictly "mess with Linux" I can achieve much more quickly, easily, reliably, pleasantly, even, in the end, cheaply… with Windows: for examplesetup a Torrent, dlna, backup, remoting… server.
The issues I stumbled into along the way are numerous, mainly me not knowing how to do stuff, not even knowing which terms to search for, nor, really, where to search for them, but also software not working as it should, non-existent/bad/out-of-synch docs… I mean, it took recompiles to get to a setup that only crashes about once a week, plus once or twice during every rsynch. And hours looking for how Upstart works (still haven't figured that one out completely.. how do I autolaunch at boot transmission and minidlna in their own "screen", or whatever screen's successor is (I forget). I still don't know why my samba setup works (kinda, it's several times slower than it should be), after hours trying to build a config file, i copy-pasted a barebones one from somewhere.
My point is, if people get a Pi to, say, learn Python, and have to spend hours installing, configuring, debugging, compiling… Linux, all the while looking for/at docs that may be out of date, non applicable, non-existent… they'll get frustrated and give up, as I would have done if UKScone had not come to my rescue when I wanted to setup a Linux home server. Needless to say, my Linux server is on borrowed time. The learning curve is just too steep and too long.
There's even a next step, which I hate to mention, of not only wanting things to Just Work, but to Look Cool, too. Think Apple: People, especially young ones, are always seeking validation. And regular people far outnumber geeks, so "hey look, I almost got my new computer to boot" doesn't earn nearly as many brownie points as "look at my Angry Frogs game". I think we need to get users to the Angry Frogs point as soon as possible. They'll come back and "mess with Linux" if/when they want to and energetically redefine the peer group they're looking for validation from.