penis head engourged

I have read here before that you should be able to have your wrap on all day. When I put mine on, I am able to piss, so I would think I have it wrapped right. However, after the first or second hang, my penis head looks engourged a little bit. It is definitely bigger than it was before I did the initial first hang. Should I then re-wrap before the next couple hangs, or let it stay engourged and continue to hang?

You want to re-wrap after each hang to restore the penis to a relaxed state and normative blood flow. It does no good to keep it wrapped for extended periods, that is more than twenty minutes. You certainly would not gain anything by extending the engorgement.