I have only once circumvented georestrictions to get a book cheaper, however I had the blessing of the author first. When the book was released, it was selling for 78p (~$1.32 at the time) in the author's home country of the UK. Stateside, unbeknownst to the author, the same book by the same publisher was selling for $19.99. The paper copy of that was selling for half of that. Since he was someone who long ranted about overpriced ebooks, and pushed for the cheap price in the UK, he gave everyone the go ahead to buy it in the UK. After what I assume was Bob complaining, the publisher readjusted the prices in the US to be close to what it is in the UK ($1.99). Even though the UK was still technically cheaper, I'd have been happy buying at the adjusted US price, had they offered it initially.
That said, it is the only time I've ever done so, and really the only time I ever plan to. I want to pay the authors of the stuff I like.