But oddly enough, I actually think the mutual coddling relationship is more destructive for Stefan. But that's a whole other tangent.

Of course it is! I'm watching 2x14 right now, and I feel all awkward, because Stefan is totally directing everything towards Elena. Whatever you want, whatever you are comfortable with, whatever is ok for you. Ok, he's being supportive, but... it seems like he has no expectations at all; whatever Elena decides to do with their relationship will be fine with him. It's not healthy for him. Hell, it's not healthy for neither of them.