i just want to throw my two cents into the ring regarding pro boards.
i don't think i've ever bought a board because it was a certain pro's board. i don't know how board royalties work (i'm guessing that they basically don't work based on "how many boards kids purchase" and is more "how many shops ordered the board"). i consider these things, in this order, to be important when buying a board: size, shape, price, brand, graphic. i've never seen a board and thought: "man, i really like that guy's skating. i was hoping to get an 8.5 but i'll get this 7.75 just because he's so sick!" that seems unrealistic.
generally, i don't notice if someone is skating a pro's board unless the board is new (read: not all marked up) or they're standing around a lot flashing that shit. if they are skating some pro's board, sweet! but i don't think that purchasing a pro's board equates to money in that pro's pocket (too bad!) - and basically, the name on a board is out of sight and out of mind when i'm skating. as far as i can tell, having a certain name on your board doesn't affect your skating.
it reminds me of middle school to be preoccupied with who's board you're riding. seems juvenile and silly. but it's all gravy if there's money in the bank at the end of the day.