He made the Scribes & Pharisees look like idiots because He exposed their pride and hypocrisy. Not because he pulled punches on calling right from wrong or speaking the truth. (though, we're to do that in love)

I think you're reacting to something I'm not about. I'm not saying we're to be "hard on sin" in the sense of being a jerk all the time or preaching 100% fire & brimstone. My point is that we have far too much dismissing of sin these days, and it leaves us with a bunch of shrugging "mistakers." If it's just a mistake, we can correct it. "Oh, oops. Mah bad." The fact of the matter is that, as Christians, we're to love Jesus and hate sin. The closer we are to Him, the less we'll desire worldly things and the easier it is to discern real worth from foolishness.

Don't confuse me with someone who thinks it's a bad idea to hang out with sinners. As you've already pointed out, we're all sinners. In Christ, we're also to be fishers of men. We have to remember that we were all fish once, too. I think it does require some wisdom, though, as weaker Christians are more prone to be dragged down than they are to be salt & light.

As far as the judging goes, I think this is another area we get mixed up on. "Judge not, lest ye be judged" seems pretty ultimate to me. So, no, I can't pronounce any judgment on someone's soul or destiny. That would be silly. An equally silly stance is that we're somehow incapable of judging what actions are unwise or sinful, and completely keeping our mouths shut about it. I see that you're reacting to people who shove their single-agenda opinions in others' faces, but I'm not one of them. If someone's professing to be a Christian, I will admonish them as a brother in the faith. If they're of the world, I'm not going to beat them over the head with what will sound like foolishness to them. If they ask, I tell. Otherwise, I try to be tactful-yet-straight about sharing what I'm about.

At the end of the day, Christians worship a homeless guy (who happened to be God) that got killed for speaking the truth. (and thank Him for rising again, lest our faith be pitied above all) People aren't always going to like what we have to say. That doesn't mean we go out of our way to be jerks, but we also shouldn't pull punches when people ask us questions like "Biblically, should I be sleeping with my girlfriend?"