Hello Kevin. I have been accepted to Michigan and on the waitlist at Chicago. I live in Chicago and want to go into finance, so I would like to go to Chicago over Michigan (although, I think the Michigan program is fantastic). Either way, I am happy to be in somewhere.
So I am in a similar situation: in at one school, but on the waitlist at the school I want to go to more. Because of this, I had to pay the deposit at Michigan ($1000) and wait to see what happens at Chicago. I am fine with that because I would pay and extra $1000 to go to Chicago. However, some people find it hard to part with that kind of money.
I have been through Moutauks book, but the one thing it does not mention during the waitlist process, but I think it is very valuable, is to talk to students who got in off the waitlist. I talked to about 5 from Chicago and got an idea of what they did. One student put together a photo scrapbook of why she should be admitted to the GSB. She said about a week after sending it in she got admitted. This influenced me to develop a powerpoint presentation about how I would be a good fit to the GSB and what sort of things I would add to the institution. I spent a lot of time on it and I thought it was good. I also sent in the additional essay and another letter of rec, which is more than what most waitlist students did. So at this point, if I don't get in, it just wasn't meant to be
One note on letters of rec. I think they are good only if they add something to your file. If it is from a boss that will more or less write the same thing that your other recommenders wrote, then it might not add much. I opted for an administrator at the non-profit organization I volunteered at, knowing that it would add a dimension to my personality not caputred in the rest of my application.
Again, I hope this helps. Let me know if you have anymore questions. Keep me up-dated on your progress.