I have one of the new Apple 30 Gigabyte iPpods. It is supplied with Music Match Jukebox version 7.5 for PC and Windows users and iTunes 4.0 for Mac users. Music Match works fine for converting all of your CD's into MP3 files and for transferring them from your PC over to your iPod.
The iPod connects to your PC via a Firewire cable and uses this to transfer the music files from the PC to the iPod. This is a very fast method of transfer (it takes around 15 seconds to transfer a whole music album worth of MP3 files from the PC to the iPod), but you will first need to ensure that your PC has a Firewire port/card installed.
Alternatively, you can use a USB2 cable, however, you will have to purchase this separately from Apple as it is not supplied with the iPod.
To answer your questions, 1, They are very user friendly and simple to use. 2, I assume your are talking about downloading music from the internet, therefore the amount of time it takes to download a song will depend upon what quality setting was used to when the song was converted into MP3 format. MP3's can be recorded at various quality settings known as bitrates. MusicMatch allows you to record MP3 files at bitrates from 8kbps to a maximum of 320kbs. 8 being very low quality but with a very small file size, to 320 being maximum quality but with larger file sizes.
It is not simple therefore to say how long it will take to download files from the internet. The average file size would be around 3 to 5 Megabytes for 1 song.
Which version should you buy, well, how much do you want to spend ? The smaller capacity 10 Gb macines are the cheapest. I have the 30 Gb machine and I have transferred over 200 CD's across to it so far (at a quality setting of 192 kbps) and I have over 20 Gb of space left.
Apple claims you can record 7500 songs onto the 30 Gb machine, but this will be with the quality set at 128 kbps.
I hope this helps a little. You could also look at this review click here or have a look at this iPod forum for advice click here