you might as well show up with the word 'sucker' tattooed on your forehead.
guys, it's 2013. if you're buying things like fancy nights out and nice dinners before you even kiss the girl, the joke's on you. also, if you're buying drinks for strangers OUTSIDE the context of an actual "drink date", the joke is also on you.
I don't think the girl is going to frame it the way you are thinking about it. She won't be thinking "he paid $50 so he could hang out with me," she's going to be thinking "I am looking for some sign of income/stability (check) and his time must be valuable because he isn't spending it courting girls online."
I'm sure it's inevitable and certain types of girls may think about it the way you've described, but when you have identity tied to everything, you can eliminate those matches from the system. You never give or receive feedback on traditional dates, it's just a black box. It goes back to how well the matchmaker does and what the person is looking for. That's how the matchmaker is reviewed by the user.
and it's VERY DIFFICULT to get that expectation out of one's head, and it manifests in very unattractive behavior (either entitlement or neediness).