Yes, the program is on there, you can use several different ones, one imparticular is boXplorer, it's essentially a file manager for xbox. You should be able to select the files in one window, go to the other and choose your destination folder, then choose copy from the menu. As to which xbox date would be better, anything not brand new or a 1.0 is the easiest, if you want to give me the serial numbers that correspond with those dates I could tell you with reasonable confidence what version it is. If you can't I think that the 2004 one should be fine, it's probably a 1.5 ( or something around there ).
Also, the only chips i've got in stock right now are allredy going in other xboxes, so if you want to gaurentee one instock, you could get me the money for the chip and i'll put in the order ASAP.