As far as iTunes, I would play around with it a little more. I've sworn by Musicmatch and have used it since the first version. I switched to itunes mainly because the remote on my audigy2 soundcard would not work with Musicmatch. Not only is iTunes sound comparible to Musicmatch, I've grown to like the browsing/organizing capabilities 10 times better.
I'm guessing from your statement that you have not found the browser, just click on the browse eye in the top right corner. If this is the case, you may find iTunes to be your new player.
As far as players, I love the iPod and really like all of the accessories that you can find in the local stores, as opposed to have to order from factory.
Edit 1 - Worth noting, if the music browser part is a big consideration, I can only say I absolutely despise the sound quality, and the organization portion of Mediasource, which is the Creative organizer, I have it on my laptop for the Sound Card and for my old Creative MP3 Player (Nomad, not Zen), actually, I really need to take it off because I find it useless, and used Musicmatch for the player transfers when I used the Nomad.
And as far as organizing with the iTunes, this is on roughly 50-60GB's of music.