As much as people dislike apple and what not, when I first started using my itouch, it was loads of fun using the touch screen flicking lists up and down and just seeing them whiz by! Not everything is perfect but macbooks definitely have certain superior design qualities compared to other companies.
Having said that, I am not an Aapple fanboy but I do see their merits.
About managing the itouch, I use foobar and there is a plug in that makes it really easy to manage the music aspect of your itouch: foo_dop not only that, it's also a lot faster than using itunes and takes up much less resources which is especially good considering how old my system is.
There aren't any problems with drm free files and I would recommend jailbreaking the device asap.
Sidenote: I am going to take the android route in the near future.