Go for whichever works for you. On my computer i use iTunes for my music, because it just works how i expect it to, whereas media player doesnt. Then when i got a new mp3 player(did have a creative muvo thingy before), i got an iPod, because it works seamlessly with iTunes, works well+easy to use, large clear screen, looks good and has plenty of accessories.
But, my creative player was better in terms of battery life(flash based, so should be expected really), use Windows explorer to put music on(no WMP rubbish), great to use as a usb flash drive too.
So realy, just get the player+software combination that does what you want to get out of it.
DOS