I read your posts, you sound like an Asian who grew up in Asia. As an Asian guy, yes, we feel that we should be paying for all dates. But that is because it is in our culture, and that is what we've been taught. Because it shows that men are capable providers (Again, culture). But of course, Asian girls are also taught to reciprocate that by being a homemaker and always gives respect to the guy's final decision. That is our 'Traditional give and take' concept. I believe yo don't follow this tradition, and instead just pick out whatever is convenient for you as an excuse.
Base on the quoted post, I believe it is quite basic to bring enough money when travel. I'm saying cash, not card. Were you hoping that your boyfriend pays for your cover fee so as to deliberately not bring enough cash? Of course your guy would be willing to pay for your cover fee. $5 is not enough reason to waste time running around for an ATM. If you buy him a beer, it should be because he is your boyfriend and not because he paid for your cover fee. And I think you wanted to be thanked because the beer you bought costs more than the cover fee, and not because of common courtesy reasons.
Based on this thread, it seems that you tend to put some sort of a price tag over for every goods and services being rendered, and that is not very healthy. You do things out of love. Otherwise, hire an accountant for a chaperon so that he can do cost analysis and gives you a report whether you or your boyfriend has overspent for each other.