The Blackjack runs a version of Windows mobile. Thats just what it sounds like, a mobile version of windows that will do just about everything and anything that your windows PC will do.

It comes with a mobile version of windows media player and as such will play just about anything that your computer will play.

I haven't used the blackjack itself so I don't know if there is a "little blackjack box on the desktop" that you can just drop stuff into. Most of the time it would show up as a mobile device on the computer and you'd sync your media with the phone from there.

The strength of windows mobile is also its drawback in my opinion. Like I said it will do just about anything that your PC will do but that also means that any of the problems you may have ran into getting something to work on your PC you'l run into getting it to work on your phone. For example even if you have all of the latest video codecs on your PC and the video plays fine the phone most likely isn't going to come preinstalled with those codecs so you're going to have to go out to the net, search around, find the right codec (in a windows mobile version) and install it onto the phone. It means you can do a lot more with it then you can with an average phone but it also means you might have to put a bit more work into getting it to work.

Keep in mind that there was a newer version of the blackjack recently shown off. There is no official release date but if they are showing it off at trade shows and such it means it should be coming soon. Its up to you on if you want to wait for that or not. I'd just hate to see you buy one only to have a new one come out a month later.