I'm an Ugly Gang Warlord. I am reminded of my ugliness on this website quite regularly. That being said, back when I was young and in college, I only received a 100 dollar stipend per month from the Navy (NROTC) that I used mainly for laundry. Women in college and some outside of college understood this. So when they asked if I wanted to go somewhere and I responded with "I don't have the money", they would say back to me "I asked you out", meaning they would pay, and they did quite regularly. These were attractive women, who a lot of times also came from upper middle class families and higher.
Now, that above sounds like humble bragging, and perhaps it is a bit. The real point of it though is to make this statement. If the women find you attractive, they will be willing to spend money on you. If they find you attractive, they will be willing to go 50/50. If they find you attractive, a lot of those requirements they say they have can be laid aside and sometimes even ignored.
Now that does not mean you should not spend money on dating. What it does mean is that if you are the one always opening your pocket for things, meaning she does not spend money on you too, then in my opinion you are no better than a trick.