yes ....use really any ftp program to ftp to your xbox....if you have a router is very straight forward and easy...if using two NICs its a pain in the ass
i use flashfxp works great and can be used for xbox to xbox transfers as well
just send them to your video folder (or create your own through the ftp program) and send it over....when you no longer want it there just delete it man
depending on your dvd rom drive ( i have an older samsung) mine will play any cdr i throw in it...you may have to use a cdrw for other drives
and if your traveling with it and staying in hotels its probably a good idea to pick up an RF connector just in case the tv doesnt have the correct ports to plug in audio and video
i have seen RF connectors rather cheap on Walmart web page to order online
xbmc will play bin , cue files as well no worries....just pick videos in menu, than the drive you have the flicks on, folder, movie, done....have fun