ugh, capitalism. someone somewhere will actually do work towards this goal with that much money in mind as a worthwhile payoff. ending tor anonymity should have at least 2 more 0s on the end of the figure.
i don't think hats are even involved here, unless we're living in a world where wget and SVN and incrementing query strings are considered crimes...wait...doh
I've been considering a markov chain + tumblr/twitter to do this. Generate an "aesthetic" and then use it to grep for products/descriptions, as well as other "content" so as to appear like meat. The more interesting part is seeing if I can write code that acts like a tumblr user...
Start with Ruby, build some command line apps. Make a chess/checkers/other complicated game to cement in object oriented programming.
Move to Rails. Learn some SQL(sqlzoo is probably enough). Rails has a lot of magic, if something seems magical learn what it does until it is no longer magical.
After that, add some javascript/jQuery to your rails apps. Once you feel comfortable with that move onto a frontend framework like Backbone or Angular.
http://ruby.railstutorial.org/ This is the go-to rails tutorial. But beware that he doesn't explain things in super fine detail, so if Hartl tells you to do something that you don't understand stop and do some research on whats happening. Expect to spend a day or two on each chapter.