Correct me if I'm wrong here please, but I thought the Hobie had the right of way being the upwind boat and if the spin is up the 20 must be going downwind.
Also, let me say I have been in a situation where I was upwind with an spin boat coming down toward me when he got close he jibed but he was so close I started to tack and I was trying to stay out of the way by we got pretty close.My thought was he knew I had the right of way but was using all his speed before changing course.
You are mixing headings with positions. An upwind boat is one closer to the source of the wind not the boat that is beating. The upwind boat is referred to as the windward boat. The spin boat going downwind must be to the windward of the beating boat before a crossing situation would arise.
And then, windward/leeward only applies to boats on the same tacks. In this case the boats on different tacks rule applies.
[color:"blue"] ON OPPOSITE TACKS
When boats are on opposite tacks, a port-tack boat shall keep clear of a starboard-tack boat. [/color]