Thanks for all the advice and such.
On #1, I think of the "pre-paying" as a "face-saving" way to say "Can you please give me money?" I just surprised myself that I did despite my trepidation and wonder if I was being altruistic or being played.
On #2, I had some OTC and BCD scheduled with her tonight. She had to cancel the OTC time due to another appointment. I find myself disappointed even though I know I'll have a great BCD session. I think the pussy gods are telling me something.