Given your description of the events (width, time to start, position, etc), Jake, I'm not sure what the need for heading you further up would be, except to disrupt your starting maneuver...
Along the lines of starting, although I don't see as many starts as others it would seem that luffing at the line is the mode de rigur. I know cats accelerate quickly, but if you're parked and have few (if any) rights what advantage is there?
I was always scared of being pushed over early. Perhaps this may be better in some cases than starting second row?
Back to Jakes conundrum... is there any obligation of the leeward boat stating their intention (such as "UP") until they actually acquire rights? With the closing speed Jake is suggesting, the leeward boat could have called earlier (but could have opened the door to Jake driving down to block)....
just thinking out loud here..