Well, this comes down to play styles and having players that game the system. For me and my group, we would absolutely prefer to do the former (a series of skill checks to hide and get the drop on the guard) even if it makes no difference mechanics-wise. The story is the thing. I agree (and have said elsewhere) that perhaps gaining advantage as well as surprise would work better.I look at it this way with an example of a typical situation... a ranger tries to stealth up to a guard protecting a door, making skill checks to remain in hiding. He gets up to the guard and then attacks with Surprise, meaning he goes first since the guard's initiative drops by 20. But because the ranger had a +4 DEX mod and the guard had a -1... chances are good that even if the ranger just WALKED up to the guard in plain sight... he was going to roll higher on initiative anyway. So all the efforts to stealth up and get Surprise gained nothing. And thus the ranger is less likely to try something cool like sneaking up on a guard if there is barely any appreciable advantage to doing so. Why go through the effort? You aren't really getting rewarded for clever play, because you're getting something you already would have had more often than not.