As a cheap bastard who is well versed in this subject, I'll try to share some things that have helped me booze it on the cheap the last few years.
Preparation:
Try to get a local paper or check out the venue websites to find out about specials and happy hours. Or after living in the same city for awhile you'll know which places have the cheapest night in town. Sometimes these cheap nights attract a fairly large younger crowd with lots of girls. Take note of the nights and venues you notice this, most younger girls don't have tons of cash to spend on booze so these events are often a win-win situation. On the opposite extreme if you know that a Monday night (for example) is always pretty much dead in your area, don't even bother going out. Drink at home if you have to on these nights and save the cash for the nights you can run game.
Pre-game:
No matter what you like, it's always gonna be cheaper to drink some (or a lot) at home or with friends before hitting the venues. For most people who drink regularly, you can probably easily blaze through the first couple drinks without even getting a buzz, and if you're already out when you do this, it's a lot more expensive to get started. Try to live within (or get a hotel when vacationing) walking distance of some venues so you can feel pretty good before even walking out the door. No matter what, getting at least the first drink or so out the way before leaving is a good idea. On nights when you're going out with a large group it may be beneficial to pre-game a LOT before even leaving and show up an hour or two later than you normally would, then take a cab where you can share the cost between several people. A longer pre-game and a few extra dollars on a cab can save you tons of money on the nights you can go in a large group.
At the venue:
I tend to stick to beer or straight drinks of hard liquor. The mixed drinks tend to be the most expensive and the added sugar in sodas and juices doesn't help your health. Drinking $12 margaritas all night will add up quick. Lately I've also made a conscious effort to drink slower while out. If you get too smashed you'll get whiskey dick, end up blacked out and wake up in a strange place, and leave your card at the bar after you leave.
Another good strategy is to have some venues where you're a regular and get hooked up. Try to get to know the bartenders or some of the staff and in some places you'll notice the tab is often much less than it should be (this won't work at every venue, try to feel out how receptive they are to you). If the bar is at some large corporate chain you're probably not getting a discount or free booze. Possibly make a venue where you know you're gonna get free stuff your base of operations.
Concluding:
If the venue turns into a sausage party (or otherwise has bad prospects) earlier than you expect it to, there's no reason to waste more money on booze. Be mindful for the entire night and when you realize there's no opportunity, either bounce to somewhere else or go home and call it a night. There's nothing worse than being at a venue with too many dudes and some random guy comes up to you and starts telling you random garbage about his job or girlfriend or something.
By following these steps I almost never go above $20-30 on booze in one night.
Preparation:
Try to get a local paper or check out the venue websites to find out about specials and happy hours. Or after living in the same city for awhile you'll know which places have the cheapest night in town. Sometimes these cheap nights attract a fairly large younger crowd with lots of girls. Take note of the nights and venues you notice this, most younger girls don't have tons of cash to spend on booze so these events are often a win-win situation. On the opposite extreme if you know that a Monday night (for example) is always pretty much dead in your area, don't even bother going out. Drink at home if you have to on these nights and save the cash for the nights you can run game.
Pre-game:
No matter what you like, it's always gonna be cheaper to drink some (or a lot) at home or with friends before hitting the venues. For most people who drink regularly, you can probably easily blaze through the first couple drinks without even getting a buzz, and if you're already out when you do this, it's a lot more expensive to get started. Try to live within (or get a hotel when vacationing) walking distance of some venues so you can feel pretty good before even walking out the door. No matter what, getting at least the first drink or so out the way before leaving is a good idea. On nights when you're going out with a large group it may be beneficial to pre-game a LOT before even leaving and show up an hour or two later than you normally would, then take a cab where you can share the cost between several people. A longer pre-game and a few extra dollars on a cab can save you tons of money on the nights you can go in a large group.
At the venue:
I tend to stick to beer or straight drinks of hard liquor. The mixed drinks tend to be the most expensive and the added sugar in sodas and juices doesn't help your health. Drinking $12 margaritas all night will add up quick. Lately I've also made a conscious effort to drink slower while out. If you get too smashed you'll get whiskey dick, end up blacked out and wake up in a strange place, and leave your card at the bar after you leave.
Another good strategy is to have some venues where you're a regular and get hooked up. Try to get to know the bartenders or some of the staff and in some places you'll notice the tab is often much less than it should be (this won't work at every venue, try to feel out how receptive they are to you). If the bar is at some large corporate chain you're probably not getting a discount or free booze. Possibly make a venue where you know you're gonna get free stuff your base of operations.
Concluding:
If the venue turns into a sausage party (or otherwise has bad prospects) earlier than you expect it to, there's no reason to waste more money on booze. Be mindful for the entire night and when you realize there's no opportunity, either bounce to somewhere else or go home and call it a night. There's nothing worse than being at a venue with too many dudes and some random guy comes up to you and starts telling you random garbage about his job or girlfriend or something.
By following these steps I almost never go above $20-30 on booze in one night.