Richmond "I'm also on the wait list. I'm not 100% happy with my GMAT score.
What do you think,
-would Chicago Booth consider an updated GMAT score if I retake it? (target > 700)
-would that make sense or is the video more important? "
1. Yes, they will.
2. Video is important
I was on the WL last year, and from what I saw, you need to show that you are interested in Booth (Video) as much as possible. It's table stakes - spend some time on it.
For the GMAT, they will take an update (they did for me last year, but I took it very late). Looks like this is an area you can improve upon, which is awesome (it's an opportunity not everyone on the WL has). Look at it as an opportunity to show you can make yourself a better candidate.
Hope that helps! I know doing both will take a lot of your time (and I'm sure you are busy), but if you want to get in they may both be necessary.