I essentially stopped reading here:

DRM can never and has never worked. You have to defeat "cause and effect" to force DRM to work. This oversight tells me you have not thought enough about the steps required to foster annonymity.

Using TOR to separate your identities is not enough. You have to ensure that each of your (virtual) machines have a different (or at least generic) software configuration as well. Advertisers (like facebook and Google) are storing an increasing amount of data. I would caution you not to underestimate potential advances in data de-annonymization in the comming years.