if you think it will bother you everytime you see it, you should pull it up and redo it before you caulk it. if you already caulked it, i'm sure no one will really notice it except you.

i wouldn't worry about water getting in between chrome and glass. it will get in there just the same no matter how close the glass is to it. my glass/chrome fit is really tight with the 3/8" tape. it actually sat maybe too high at first, but water and pine needles still get in.

the reason i said to redo it if it bugs you, is, there will always be some imperfection somewhere in the car, and chances are, you will be the only one who sees it, but it will still be really annoying. if it is something you have to look at all the time, you will always wish you redid it.

i always see horrible things in my car, but people say it looks nice. if someone points out a problem to me, they better be willing to fix it for me.