Jumping is in. It's no problem after awhile. I have found landing any unhooked jump that is spinning to be very difficult, though.
Almost the higher you go, the better, cuz you can see what is going on.
You want something bright on your board so you won't lose it.

I haven't had any problems with anyone giving me a hassle riding at night yet.
I use to windsurf North Shore park "back in the day" (night actually) before they cleaned up downtown. That was fairly sketchy a few times.