So for me personally, 100k is max threshold where I wouldn't let money be a bigger influence between choices. A diff b/t 100k isn't so bad as compared to say 200k. W/ Step 1 being P/F it's a bit more important to get through your pre-clinical and hit rotations and take STEP 2 so you actually know what you are competitive for and can begin to redirect if needed. Also, knowing my personality clerkships is going to be rough for me, and having them be P/F will reduce so much stress. My main personal concern is nurturing my metal health during schools, any conditions that benefit me mentally I am going to rank way above any other factor. If I am not feeling great about my situation and where I'm at then I will simply not thrive. I'd choose To me it's between Vandy and UChicago. I could have good classmates, and live in a nice area but if school's stressing me out, neither of those two good things will make me feel better about life. Conversely, if I am able to manage school then I can the best out of a less then optimal location and/or people (to an extent). But that very dependent on you and what your needs are.
One more thing, based on your other important need to have dating options, I encourage you to maybe talk to people who can give insight on that area in both cities. Not mitigating your want for a partner (cuz same lol), but at the same time make sure your decision isn't solely based on something that may not happen tbh. Life is unpredictable, and oftentimes the best thing you can do is focus on the present and the factors you have a considerable amount of influence on. Finding a good, compatible partner is really out of anyone's hands, and it can happen anywhere, anytime. But certainly, you want to be in an environment where you feel respected and included, and that is more than reasonable to want.