A compromise, one of many, necessary?

So i've been sort of following this minor debacle in hfx where some folks had an offensively themed party and then didn't respond well to the suggestion that they were being shitty. (http://unbeatablehigh.blogspot.com/ march 18-21)

I recently had a similar situation where i tried to call someone out on using the word "faggot" inappropriately. It was a long, painfully drawn out conversation, which started with that person arguing that people just "shouldn't be so sensitive" and ended with him finally conceding my point and, hilariously, whining about how harsh i'd been with him. Apparently gay people shouldn't be so sensitive about him reclaiming slur words for them, but he's totally allowed to be sensitive about having his privilege and ignorance pointed out to him. Right.

So anyway, i've been thinking about this thing a lot, this "what is the correct amount of 'harsh' to use on people who are somewhere in the range of ignorantly offensive to blatantly and deliberately offensive?" question.

I think this is what i've got it narrowed down to:

1. People who are using oppressive language are not the ones who deserve sympathy. Everyone is capable of thinking about the consequences of their actions and they should already be doing that.

2. That being said, i think it's possible to tell someone clearly that something they've done is offensive or inappropriate without decimating them. I feel like there's times when i need to be reminded to think about my language (i had a good conversation lately about use of the word "crazy" in daily speech, ie) and i know that it doesn't take much to make me rethink my actions, and that a really harsh judgement would probably just make me feel really guilty and awkward and miserable when that's not necessary.

3. That being said, if you're gentle and someone doesn't get it, it's fair and necessary to step it up.

4. THAT being said, even if i think someone does deserve decimating, i've learned that the more you humiliate someone, the more reluctant they are to admit they're wrong. Especially in situations where the person you're calling out isn't a friend and their friends probably think their behaviour is fine, they might easily react by just disagreeing with you. If the goal is actually to make a person stop being a douchebag, this means that some degree of tact is necessary. All-out attack will probably just enable them to write you off as a psychopath or fascist or whatever.

5. So even though i sometimes fantasize about bottling people like that, i try to be as approachable as i can when i'm talking to them about their behaviour, even if i think they're being incredibly inconsiderate and deserve no sympathy whatsoever. The situation extends beyond me and them and i don't want to reinforce their already somewhat present disrespect or even hatred of whatever group they're disrespecting.

I think the conversation i had (referenced above) barely managed to be a success, only because i barely managed to reformulate my rage into something more like bluntness. Despite the fact that this person didn't deserve to have their hand held through the process of admitting they were wrong, that was probably the only way to get them to admit they were wrong, which was my goal.