When I was snacko, we kept losing money from our snack bar. I noticed that every Thursday morning we were light. The cleaners came thru every Wednesday night, gee I wonder where the money is going. I made some signs that said this area is under video surveillance (because the boss was nervous) and set up the squadron video camera the next Wednesday. Thursday morning, the fund was light again and the video nailed the cleaner. We gave the tape to SPs and the same cleaner wasn't cleaning the next week.
We pretty much do most formation debrief in the bar over a few beers. If you screwed something up, you owe a round. Make the bar everyday user friendly. We have a computer with a power point hog-log running on a plasma behind the bar. You add pics from your most recent TDYs/deployments- it's usually funny stuff and keeps folks laughing.
We used to have a quarterly party with different sponsors. Pilots take a quarter, loads take the next, support has a quarter, and leadership has the last. Maybe a burger burn, shrimp and crawdads, brisket, etc. Each section pays for the party food but the bar keeps the profits on beer and anything above cost.
You want to sell items with a great profit margin, that means buying cheap or in bulk. A drink that cost $.25 to buy and you sell for $.50 is better than the shirt you buy for $12 and sell for $15. You'll also sell many more drinks than shirts. When you order merch, keep in mind you'll only sell so many shirts, hats and coins to squadron members, so don't tie up too much capital with a gigantic order that you won't sell out of until 2012.