The following two statements are very much at odds with each other:

I apologize for being blunt, but you did not succeed in crafting the situation you're aiming for. It was VERY close. W was not deliberate. To me, it was indeed clear that W was not keeping clear... it required a hard luff just to avoid contact.

Sailors regularly push the boundaries of avoiding contact without taking into account their need to allow others room for RRS 14, plus the other requirements of keeping clear. It is this issue which causes sailors to feel like judges are "defaulting".

Yes we've used W finishes for many fleet events.  It works well for the back of the fleet. Not entirely sure the front of the fleet would be thrilled at having it used if they weren't 100% sure they were being recorded at the front.

I realise handicap racing is not popular on this board. For reference - W finishes are not appropriate in handicap races as you need to adjust time and 'distance' (laps).

I would second that for people on a Mac!!

The more I think about this ... the more the reptile-level of my engineering-brain is whispering to me that the only way that this ILCA gets back to its original position + improved position on the line ... after countering the losses due to wind and water drag forces ... and the leeway loss when the sail is initially brought in ... without passing HTW ... is by the input of energy from the body resulting in a fan of the sail (and skeg). 

Call it just a conservation-of-energy analysis instinct .. I'd have to break it down to each dynamic segment to see if I'm missing something. 

I will return (with trepidation) to my original stance.  In this scenario, unlike on a beam reach for example, I contend that there is only one side that can be chosen by the ROW boat to pass the obstruction and where, therefore, RRS 19 applies.  Blue can chose head up and go behind Yellow.  In this instance, I think we all agree that the obligation is on Green (RRS 19.2b) to give Blue room to pass between her and the obstruction. Blue's obligation (RRS 19.2a) is to give Green room to keep clear as she changes course.
If, however, Blue choses to avoid the obstruction by gybing, she is not passing the obstruction .... indeed, she is not able to pass the obstruction on her port side unless at position 1 she suddenly had a burst of speed and could cross Yellow.  Given that she is unable to pass the obstruction on her port side, she chooses, instead of heading up to pass on her starboard side, to avoid the obstruction by gybing.  Therefore in this instance, RRS 19 does not apply.  Returning to my original post, I believe this is why the language of 'pass' is not used in RRS 20.  

In RRS 20 (sailing close hauled or above), there are things that have to happen for the ROW boat (leeward) to be able to safely maneuver to avoid the obstruction (again, it doesn't say pass).  Should she chose to avoid the obstruction by tacking (rather than passing it astern per RRS 19) she has to follow RRS 20.1 and things unfold from there.

In our scenario, it seems to me that if the intent was that Blue had obligation to give room for Green to gybe between Blue and Yellow (obstruction), there would be another rule entitled ROOM TO GYBE AT AN OBSTRUCTION with a series of hails and responses.  This would be problematic however, for all the reasons that I stated in previous post (broken overlap; uncertain duration of right to room, etc.)  However it seems to me that this is NOT the intent since the ROW boat  going downwind already has the ability to execute the choice to avoid, rather than pass (which they don't going upwind without the protection of RRS 20), and the give-way boat already has the ability to pass the obstruction safely by heading up astern of the obstruction.