I've been sending TV shows to friends privately since I started using dropbox. Never seen a takedown. As long as they don't get a dmca, I doubt they care.
If they did how hard would it be to pad media files with some salt to break hashing anyways? Not hard at all...
Pro tip: You can usually get away with entering invalid similar characters on recaptcha when the word is really blurry. Substitute 'ri' for 'n', for example.
I like to do this as a game, to see what I can get away with, adds some fun to the drudgery of typing in a captcha.
Hmmm mac only for now. I'd be able to try this out with Linux and Windows versions. I have a mac, but it usually sends files to non-macs.
What's the advantage over Dropbox? Does your service go through a central server, or is it more p2p? Or both? Are my files encrypted on your server? Storage or bandwidth caps?