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Syncing Video folder that is Larger than my Drive

I have an HTC rezound, and I am working out a way to sync my video files. I have a large folder where I have ripped all of my TV shows, and I have 40+ GB's of files. In my phone I have a 32gb microsd card which is solely for video storage (my music is on the internal drive).

My question is this, is there a way to set my system up so that any time I plug my phone (or run a program), it randomly syncs 32gb of videos to my phone. Basically I want to keep a fresh selection of videos on my phone from my rapidly growing video collection.
 
I would think the best you could do is a PC program that would select a random set of videos with some maximum user-defined total size then copy them to some other location, like your phone's SD card mounted to your PC. It could clean up your phone's video directory as well. I'd think a competent Java programmer could whip up something like that pretty easily - depending on how fancy you'd want to make the user interface.
 
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