It does sound interesting. I think I would grill some chicken and then have the caesar salad as a side dish to go along with it. I have never tried grilling romaine lettuce but I do like how Booby Flay brushes the leaves with oil and give them a little seasoning. I think I would by pass making the dressing unless I have a lot of time and ingredients. There are just too many good ones in bottles that I can simply buy instead.
Wow, I would have never though to put chipotle in caesar dressing. Not sure how that would taste, I might try and whip up a small test batch to see what it tastes like.
I enjoy grilled lettuce from time to time. You need a screaming hot grill to do it right though, indoor ones don't seem to get hot enough and just wilt the whole thing. When done correctly, it's a nice mixture of textures.