First message, is there a work around?

Pretty good system I think

Prevents

First message: Hi!
Second message: Say Hi to my dick as well

Interact with them on a post. Then add in, "Hey, I DMed you." If they still don't respond, then be respectful and realize they don't want to talk.

No you just got to wait. I think its fair.

I doubt it. I prefer this. Self-service block mode with minimal effort required.