I have some points of specific advice, but overall, I think you just need to relax and stop putting so much pressure on yourself to find a girlfriend. As much as you'd like to identify a problem and fix it, sometimes dating just comes down to whether you've met the right person or not.
Having said that, there are some ways in which your attitude isn't helping you.
No one cares how much money your daddy has. It is literally not impressive at all. (I mean, why would it be? You're not the one who earned the money.) The number of times you brought it up in this post makes it clear that you feel this is a point in your favor, but it's not. You say you "could give a girl a life she could only ever have dreamed of," which honestly made me laugh out loud when I read it. Do you think girls sit around dreaming of the expensive restaurants they wish some guy would take them to? (Hint: they don't, at least not the ones who are worth your time.) How you make someone feel is 1000% more important than the nice shit you can buy them.
You've made the common mistake of thinking a girl owes you something because you took her out and were nice to her. The fact is, she doesn't owe you anything, and if spending a lot on dinner only to be rejected is making you bitter, stop taking girls out to nice places. In fact, you should stop doing that anyway, because...
Expensive early dates put too much pressure on things too soon. Some of the best first dates I've had have been walks in the park. Getting drinks at a bar is a good first date (once you're 21). Dinner in general isn't so good because it's kind of a high-pressure environment for making conversation (staring each other in the face instead of sitting or walking side-by-side, and trying not to eat like a slob). And spending a lot of money makes things worse. It's an overly obvious way to try to impress her. I mean, you wouldn't hire a limo and a string quartet on a first date, would you? Well, going to a really fancy restaurant is overkill for the same reason.
Anyway, this was kind of long-winded but you're doing better than a lot of guys you're age: you're not afraid to ask girls out or show them how you feel, which is great. If you stop trying to impress girls with cash, you should be fine.