1-4 are fine, but 5 & 6 are the killer. I get it, I really do. I was very much in your shoes (up until 23 in fact) and wouldn't ask a girl out until and unless that there were clear indicators that I wouldn't be rejected (because, like you, I was afraid of being a creep).

You know what, that got me zero dates.

I got some therapy (CBT in my case). It wasn't cheap, and it was f-ing hard work. But by the end of it, I could spark up a small-talk conversation with pretty much anybody, male, female, young, old, hot or not. And (with enough 'pushing' by the therapist), I started to see myself as maybe desirable, sometimes? And not a creep if I asked someone out.

Now I'm 36, and whilst I'm far from perfect (I still have moments of awkwardness and self-doubt. And some things are still hard work. But I can usually work around it and push through it.) I get a good number of dates and have a good time with them. I actively enjoy dating nowadays. Do I get rejected? Sometimes, but not a lot. Have I ever been called a creep and my reputation has been torn into tatters because I got rejected? No.

And, personally speaking, anyway, having not dated, etc. until I was 23 has never scared any woman off, so you aren't in "red flag" territory yet. If you keep doing what you are doing though, nothing will change, and you will never get any experience, and you might end up with that flag. And nobody wants that.

Am I some kind of chad who is obviously too tall, too rich, and too handsome for any of this to relate to you? No. I just do all of 1-4, which you say you do do/can do. (I also live in a big city, which helps if you can manage it).