Thinking of getting an iPod. Couple of questions re iTunes?

Personally (and the general opinion) is that Apple rule the world when it comes to MP3 players. It is very rare to find someone who has not fallen in love with their Ipod. It is a simple as anything else you will use, yet the quality is far superior. You WOULD need to put you collection through Itunes but I now have 12,000 tracks and still adding and its an amazing `jukebox` for myself, parties and friends to browse and borrow. Also, as Apple lead the market and new ideas will always be on the ipod first. In a nutshell, WMPlayer is a poor mans itunes, and once you have sussed its basic workings, you will never regret converting to itunes.