This is pretty much where I am headed. I already built a plex server and am in the process of downloading digital versions of everything I already own on DVD/BD. So for now I don't consider it piracy since I already paid for them, I'm just grabbing someone else's digital copy instead of making my own.

Once I'm done doing this though, if "big media" isn't ready to offer me some kind of all in one package for streaming, like what netflix tried to be (and is now failing horribly) I very likely will head towards to high seas.

The general rule is, if you want to prevent piracy, the paid experience has to be simpler and better than the pirate experience. So far when it comes to video content, this doesn't exist. For gaming however, Steam is doing it (mostly) right and I have not felt then need to pirate a game.