Just my personal opinion here. If one looks at a rule, one should also be trying to understand the spirit of the rule, which is generally trying to avoid allow an unfair advantage. If one starts to immediately look for loopholes around the spirit of the rule, I see that as looking for a way to rig or cheat the system. To me, the spirit of the rules is a big deal. May not be a big deal to others.A loophole is, by definition, not not following the rules. It is allowed by the rules. That's the point.
As I mentioned in a different post, I actually know a guy who insists that "If you aren't cheating, you aren't trying.". That attitude, at least to me, is one reason we keep adding more seemingly ridiculous laws and rules to an already long list of laws and rules. We try to keep plugging loopholes because there are some who just don't feel they can be successful if they are forced to compete with the exact same set of standards as the guy who's already reached the pinnacle they're striving for and will always look for a way to find a shortcut. I don't have any specific names or situations for you (I'm sure everybody else can come up with several to discuss) I'm merely speaking of the concept.