I use iTunes to import my music, then transfer to the iPod. It's easy. Basically setup so a child could use it.
I have over 400 CDs (and 2 hard drives full of music from a DJ buddy and another buddy that's a bar owner), so I imported all of them onto my NAS drive. Then, I just use iTues to skim through and add/remove music.
Get Electrical Connections setup for it. I have the old version that requires a separate wireless controller, but I like being able to see what is playing, coming up next etc.
If you don't have CDs and don't want to spend $10-$20 per CD or $0.99 a song through Itunes try www.gomusic.RU $0.15 a song, 10% off if you buy an entire album. They don't have everything, but a lot of good stuff there.
There are still lots of places for "file shareing" on the net. Go to your ISP and see if they provide access to a Usenet or NNTP server. This was how people communicated prior to forums. There are sub directories for every genre you can imagine. Option two is do a Google search for Bit Torrent and follow the directions. I do not advocate or promote either model, only offer this up as information from a Geek.
I resisted iTunes for a long time until my nephew convinced me to get an iPod Touch.
The current version on iTunes has something called genius mode. It will create a playlist based upon a song you like. Its very cool and works surprisingly well, especially if you have a large library of different kinds of music.
I have been using a Apple Ipod for three years now... Once you have your Ipod and set up an Itunes account for free...You then have the option to buy music from their site(Itunes) or load your own CDs on your personal library on the Itunes site from there you are able to download the music onto your Ipod from your Itunes Library...I haven't tryed this,but I believe you can load your CDs onto the Ipod without going through the Itunes site
You don't even need to buy the music... You can use a Torrent downloader and get entire albums for free. I import these into iTunes, select only a certain number of songs off each album and delete the rest. I have a Mac, so it always works...