I agree with above that some of that **** seriously doesn't matter. The $3000 difference in salary per year or the 2 free white coats will not make up for being in a malignant program full of condescending sociopaths.
If your goal might be fellowship, then there are some things that matter I won't list. Like time for research, presentations, meeting attendance, prestige, etc.
If your goal is just this residency, then go where happiness is.
1) you will survive this residency, the people are supportive, they don't fire people, the politics are OK, the attendings/fellows/seniors offer enough support that you will not be left alone in the ICU with a patient dying on you and you get the blame ending your career
2) you can stand the hours, the schedule re: rotations, call, etc.
3) you can get **** done at this program, the ancillary staff like social workers, psych, behavioral health, clinic, EHR (getting **** done and not having a lot of bureacratic BS on your plate is what will let you stay sane and go home to sleep, BIG factors in happiness)
4) once you've gauged if you will ever have time outside the hospital re: eval of the above, how's the weather? Granted, you won't have much time to enjoy/hate it, but think about your commute is really what I'm getting at
5) commute
6) parking
7) cafeteria, caffeine availability
8) housing
9) on the rare time I have off, is there anything to do in this city? at the least, are there some OK restaurants? Because if nothing else after a 16 hr shift, it might be nice to have a nice meal, we all gotta eat, and that's low energy.
What matters in the life of a resident? Getting to/from work daily, hence weather, traffic, housing, parking. While at work, getting **** done. This is why the attending/senior support matters. This is in the form of orders and notes, hence the EHR or lack thereof does matter. This is also why knowing what's up with ancillary staff like nursing quality and SWs, placement issues. All of the above effects when you get home and how much sleep you get. Last, and not least, although it may be the last thing you do the whole day, is food.
Obviously if you have spouses and kids then there's more to the list.
Money won't be an issue unless the city is expensive, you don't live within your means well, you have certain expenses outside being single (medical, kids, certain debts), you need/want to buy a house, commute and family plays into that.
Otherwise, you won't have much time to spend money. My advice if no other factors, live as close to work as possible so as to not spend your precious sleep minutes trapped in the car or long public transport commute. Better to drive to the "fun" stuff a few times a week than to fight traffic twice daily.
Financially I will say that the health care plan, don't assume it's good because you're all docs and there is a serious lack of info on it and most people are too healthy to care.
If you're planning on births during residency, that will matter. Premiums, out of pocket maximum, copays, prescription coverage, vision, dental, PT, if the insurance allows you to see providers OUTSIDE your home system.