The main reason i bought my ipod was i was sick of having cds in the car. i have a wire from my car cd player to my glove box where i plug the ipod in and control it all from the head unit. Simple

i leave the car and take it with me - therefore less things to get stolen. BUT the one night i forget to take it out my car gets broken into and its taken

I now have a 120gb Ipod Classic and got myself a ipod video converter so any films, videos, programs i want i convert and stick on the ipod so when im on the train / bus what ever i can either watch something or listen to the music. Also has a fair bit of music on it - think ive used 8gb and ive 1000 tracks & about 8 hours worth of top gear, Australian top gear, prison break etc.
I have to say itunes IMO is utter shite but its simple to use. Drag & drop the tracks you want to the libary - plug the ipod in and click sync = done. its that simple!
Sony, Creative and few other brands do do good players but i think Apple are the market leaders for the simplicity of there product and easy use

If your not sure go to a apple store and look at the different ones the staff are really helpful

Also just to add there is a store on ebay based in hongkong that sells refurbished ipods with apple warranty. I got my first one from them and never had a issue at all

was at least half the price aswell

HTH
Kev