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when it comes to bars, the best ones ime only open once a week or less (especially punk live music bars). a local dive bar that only opens once or twice a month will attract different crowd than some daily bar.
far as your "demographic" goes...where are you at if you don't mind me asking? there's always an underbelly of working stiffs in any area, rich people don't clean their own toilets or prepare their own food...somebody in the area has to be working to maintain/service everything
dude none of that exists where i live. there are no dive bars. sounds like you live in some rustbelt place where rent is dirt cheap.
the working stiffs don't live here. they commute to here from 2 hours away. they can't afford the housing prices. they also think i'm a douchebag because I can afford the housing prices and I go to fancy douche bars. the bartenders and waitstaff all commute in from places 2 hours away. my dog walker commutes in from 2 hours away, etc.
and i'm not going to move 2 hours away. I love my job and I love being 15m from my office.
chicago
i've been there several times. i can buy a 6000sq ft mansion there with what i pay for a 2bed 600sq condo here.
then...why stay where you are? it doesn't sound like your happy wherever you are