Trailer Park,
This is the kind of advice that you won't find anywhere else, and it's damn good advice, too.
Overspending, whether it's a cien at the BM, too expensive a meal or too lavish a gift doesn't make you a big shot, a hero or sexier in the eyes of the chicas. Being a spendthrift marks you as a sucker and a fool.
My failing was that I used to consistently gave money to beggars. I thought it would be a Christian kindness and also keep them off me the next time I passed. Man, was that stoo-pid.

Instead of keeping the little bastards away from me, they mobbed me worse the next time, and when I gave a few small coins, they called me names and made the ugly face at me. The farthest I will go with chica gifts is a small (s-m-a-l-l) propina for good service, a piece of candy or a cigarette.
When taking a girl out to eat, never ask her where she wants to go. You're the man, in Latin American culture you are expected to make the choice. If you're smart, it will be a meal at a soda or other inexpensive place. If you want to take your novia out to a nice place, save it for a real occasion, like your last night in town. Anything really valuable (over U.S. $20.00) should be used to barter, rather than gifted to her. And finally, do not send money.
Just my semi-newbie-rookie opinion.