>>2 I may not be the best guy to give advice regarding this.. but personally I just always go for it. I've been rejected plenty, but I've also started dating someone because of it.
The way I see it, if they reject you and react badly, then that's a person I'm glad to have out of my life. If they reject me, but also can put that aside and remain my friend, that's someone I can respect and trust. And if not rejected, then awesome!
I've always taken the easy way and just texted my crushes that I liked them and then it goes from there. The best thing is to just not be afraid of rejection. It's always worth a shot, you never know what could happen.