Leaving work is really weird. I've been out of school for a while, and at my present company for the past four years. I like it there, but don't think it'll be possible to go back to the job I have currently. Like you, no one at my place of work (with the exception of two coworkers/close friends) knew about my law school plans until I gave my notice on June 23. I'm looking forward to my month off to do stuff around the house, relax, and get ready.
I think you should prepare speaking points, and call Anne Wilson tomorrow. Tell her you're still very excited about the possibility of attending Southwestern, and would like to schedule a visit -- and then ask her for a convenient time for you to fly from Atlanta so that you can meet her in person. In my opinion, if you did this BEFORE you asked any questions related to your chances of admission from the waitlist, that would send a strong signal that you're super interested, and very serious.
BTW I was just in Atlanta last weekend --- my in-laws are there. I'm a proud UGA alum. I absolutely love it back there... but I love it here too!