Based on your responses in this thread it seems like maybe you're missing that there are going to be women out there who like you as a person but don't want to date you. There's no way to prevent a woman from deciding she'd rather just be friends if that is how she feels. The classic fault of 'nice guys' is thinking that a relationship is the product of following a specific protocol. Then when they don't get it it feels like a betrayal. It seems like you're OK with rejection which is great but you do still seem to think there is a special trick to getting the woman you want. One of the most important things you can learn about dating is that there is no true protocol, that coming correct is just a thing that keeps others from writing you off immediately, and that even when you do everything 'right' a relationship is still dependent on the whims of another completely autonomous human being.

Think about it this way: think about how you would ideally want a woman to approach you if she were interested. What would she do? What would she say? Would she be direct or wait for you to make a move? Now imagine it's a woman that you are definitely not attracted to. Does her following your protocol really make a difference? Maybe you feel worse about rejecting her but I'm guessing otherwise it does not.

Since courage does not seem to be an issue for you my recommendation would be to focus more on finding women you can make a connection with. You say you've heard you should spark a small conversation before you ask her out. What is your goal with that conversation? Simply to have it? To entertain her? Or do you try to find if you have something in common. I don't know your whole process so maybe I am way off base here but it seems like you maybe you are going a little too far in the other direction with how impersonal you are making it. When women complain about "nice guys" they are not complaining about every guy who has ever done a nice thing for them or gotten close before they made a move.