My vote for a truly free hand-held platform is the n900[1].
It's beautiful, clean and comes with with Debian based distro, Maemo.
My opinions about apple were never positive, probably because I'm only 25 and did not program in the 80's. I've only saw apple as a manufacturer of shiny, well designed rich boy toys, but that is probably because I live in Brazil, where only rich people have it and they think they are 'computer people' because of it.
I was always more influenced by the open source community, and apple's record is far from shiny on that aspect.
My 2 cents.