On the nature of offensiveness in semantics, and appropriate policy

What is "offensive?" Is it the same as insulting, and is it automatically reprehensible? According to Merriam Webster's, it's what "causes displeasure or resentment". According to the Wictionary, it's something "arousing a visceral reaction of disgust, anger, or hatred". Is there more to "offensiveness" that that? Are there connotations I am missing?

Note that I'm not specifically interested in TV Tropes policies: I'm asking the question in general. When there are many alternatives to presenting an argument, is the least offensive one always the best, most effective choice? When is it worth it to disregard the displeasure of one group or another?

Also, there appears to be at least one demographic that are often offensive by sheer accident, and, what could be worse, think it doesn't or shouldn't matter. I think we have a trope for that.Or three.

edited 28th Feb '12 8:17:12 PM by TheHandle

Offensiveness is the breach of a norm. The more widely held among the receiving groupe, and the more importantly held the norm is, the more offensive the act is considered. Now, whether norms are good or evil, and their transgression evil or good in response is an altogether different debate that very probably can't be given a definite answer.

As an aside, what the hell is wrong with that website you linked to? The suffisance, smugness and sense of entitlement that ooze from those articles are positively blistering. And, funnily enough, self demonstrating. Why are [we] unpopular, despite being so much clever and "deserving to win"?