No, because you're beer can racing. Beer can racing "rules" indicate it is done in a spirit of relaxation, not "go fast." Learn to race comfortably in your beer can races first, the question will answer itself later.
Answer #2 - Nope, it's behind the mast, what difference will it make?
Answer #3 - Slugs make raising your main much easier.
Answer #4 - Look around at other boats.
Have fun, that's what beer can racing is all about.