I currently own an Archos XS202 music jukebox player. Previously I have used a Zen Micro jukebox which was faulty several times (but that's another story …) and an iPod mini which sadly I lost. My Archos is my personal favorite MP3 player I have owned for a few reasons – namely size and its folder capability.
When I owned my first MP3 player the iPod mini – which I was very happy with (up until the point I lost it) I was forced into using the iTunes software to handle my music. This meant that when I upgraded to the Zen Micro I was in a sticky situation – how did I get my music across – unfortunately for me I decided to use windows media player which was painfully slow at transfering and did not really integrate with the player well at all. So when I got rid of that and got my nice new XS202 I went back to using iTunes to handle my files at least.
The first thing I did to make adding music was easier to set up a smart playlist which allowed me to see the latest files I had added to my collection. The rule I used to create it was "Date added – is in the last – 2 – weeks" and I checked the box which said live updating.
Now this shows me the latest songs I have added to my library. When I first updated my XS202 I went into the folder which I store all my MP3 files in and then copied the file structure however now if I just want to quickly add a few songs a little know trick is that you can actually right click the file in iTunes go to copy and then simply paste it onto your jukebox – this with the automatically updating playlist means I can update the library on my Archos in minutes with my latest tunes.