We don't usually go out drinking, but when we do, we try finding the cheaper places. The closer the bar is to the center of the city the more expensive the drinks get. But if we choose a bar that's located on the outskirts or on the little hidden streets the drinks are a lot cheaper. If going out, would you rather pay more for the privilege of drinking in a nice location or are you ready to drink in cheap looking places in order to save money?
It really depends. If I'm intentionally going out for drinks, then a cheaper place is likely best. If I'm really going out for good company, like at a nice restaurant, though, then I don't mind simply having a glass or two of wine that's on the more expensive side. I wouldn't want to "go out drinking" and having lots of drinks at that price, though.
It bugs the hell out of me to pay an arm and a leg for drinks at bars. I like to drink a lot, and some of these places charge you almost the half the cost of a whole bottle for one cocktail and they only pour about an ounce of liquor in the drink. I refuse to pay $7 for a freaking Bacardi & Coke when a whole bottle of Bacardi is only $14. 2 drinks, and I'm paying $14 for *maybe* 3-4 ounces of liquor? And that doesn't even include the tip, give me a break. If I do go out to a nicer place, I will hold off on drinking too much there, usually only one drink max if I have on there at all - then we will usually go to a dive bar to get drinks. We did this quite often when we were out in Vegas, we would always go off the strip to get drinks.
I tend to agree with Jessi on the paying for a nice wine idea. I am willing to pay more if I am dining out and want to enjoy the experience of the meal and ambiance. As far as going out drinking, I find that pubs are usually cheaper than nightclubs. Draught beer is cheaper than bottled. If it comes in a martini glass and it is not gin and olives with a hint of vermouth it is overpriced kool-aid. Most of the clubs are located in one area of our downtown core. Most things outside of this zone are considered pubs with different hours. Often the cheapes place to drink is the one that has a special on your favorite beverage. With enough places to go downtown, during the week at least one bar will have a special price on alcohol for the evening.