One of the things I respect is people who are able to carefully read a set of rules and use it to their advantage. Porsche racing in the 1970s was a masterful example of this, and the Patriots/Belichick are great at it in from 2000-now. As a finance person, I've employed the same tactics at work many times, and look at it as a game or puzzle. It's something I also respect politically; I've never understood the accusations against the rich or corporations who use the tax code to their advantage*. Frankly, I always look at people who get upset over it as 'weak' and small minded, and I've always felt that, rather than complaining when someone outsmarts you with rules available to everyone, you should be embarrassed that they thought of it and you didn't. I think there's a little bit of right/left politics at play here; (warning: gross generalizations ahead) it seems like the right is more about "here are the rules, go try to maximize your gains within their bounds" and the left is more "well that guy did something the rules didn't anticipate or aren't what the rules were meant to be, that's not faaaaiiiirrr!"
*Politically manipulating the code is a different story