If you're going to anthropomorphise, it makes more sense thinking about NeXTSTEP turning into a hip Mac OS X teen - but a somewhat immature teen not yet prepared (at least according to some) to enter the enterprise world.
In case you're not inclined to follow the link above, here's a quote that I think pretty much summarizes why no multi-national IT department on the planet buys Apple products without qualms:
Just remember if you buy Apple for your enterprise, you'll be on your own. The products are great, but they come from a dyed in the wool consumer company which more and more butters it bread with products like the iPod. Consider yourself warned.
As long as people have reason to think like this, Apple won't make any inroads in the corporate market - much to my regret.
Apropos the enterprise market (and seamless Borg, er... Windows interoperability at the application level), the interesting thing is that Mac OS X might get virtualization before coming of age, although my personal bet is that this thread in the Q support forum might get there a bit earlier (provided they can get access to the xnu source).
Incidentally, thanks to everyone who's written in with advice for my sinus trouble and flying. Despite my ingrained distaste for medication, I'll be packing some counter-measures, although I have a feeling the headaches will have more than just one cause...
His tale, coupled with the usual difficulties of buying Apple products in Portugal, has made me re-think the whole issue of replacing my iBook this year - and I'm sure a lot more people are in a similar situation.