I'm glad you are up for the task of contributing! :) I pretty much don't support Windawesome any more so people are needed if the project is to stay alive. :) On to your points:
1) This is already available, you just have to activate a workspace on the other monitor.
2) This too is available and works pretty much as in xmonad - see Windawesome.SwapCurrentWorkspaceWith.
3) This is also implemented - Windawesome.AddApplicationToWorkspace and pass "follow = false". :)
4) This is highly non-trivial. We are talking Windows here and drawing non-client area stuff is definitely not easy. You could try reading here and there and maybe you could find how.
5) This, again, is really complicated. Well, maybe not that much, but it requires (probably) massive code changes and I haven't had the chance to try it. Feel free to poke around and try it. :)
So, please be my guest and implement as much as you want. I've made Windawesome as generic as possible but still for my taste, so maybe there's stuff people don't like. :)