No, I'm not disagreeing with Herb, whose assessment is spot on as usual. And your ability to notice the red flags is spot on also. I'm just thinking about how beneficial it can be, for the SB, when she trusts you to take care of her. Two recent examples from my experience: My sweetest 25 yo SB is slim, super hot, and seems to really like me (go figure!). We've been dating for over a year now. She told me not long ago that her favorite winter sport is snow boarding and she can't wait to get back on her favorite mountain, about a 2 hour drive from my home. She wanted a season pass, and mentioned I could get her one instead of our regular allowance for one visit. Well, no way I was going to be cheap with her. I got her the season pass, and I also got her a $250 motorcycle helmet she needed, which was a total surprise, and of course I also gave her our normal ppm allowance. She was very blown away, and is now talking about overnighting with me to the ski resort next winter and would I like to go with her!
I got a text from a SB I was regular with several years ago. She's a super cute Latina, just 4'11". There's something about tiny girls that drives me crazy! Anyway, she asked me for $40 to help her out of a jam. I said nope, $40 is not enough and instead I sent her $100. She's eager to show her appreciation, if I can just find the time to squeeze her into my schedule!
These are small investments which will pay big dividends in the bedroom! My point is that when there's real mutual trust established the payoffs are great for both parties. When a SB demands $ in advance she's actually sinking her own ship.