Good point. If you read the Harper's article [0] about the Joan Ginther, the "luckiest woman on earth" mentioned in this thread's top comment, she seems to have gamed the system basically by having an inside man or two (while also being good at math).
The Philadelphia Inquirer did a better job on that story. Nobody "inside", just using all publicly available information to "count packs" and piling up tax write-offs (click through to all three articles):
[0] http://harpers.org/archive/2011/08/the-luckiest-woman-on-ear...