Subject: variations in sonic boom under perfect-unusual circumstances

If a commercial air-line pilot hitched a ride on an unusually strong jet-
stream, whose speed was 300mph while his air speed was only 500 mph, would 
a ground-level observer hear a sonic boom?

If so...and an extraordinary pressure gradient existsted between two 
ground level observers [the kind that spawns spawns tornadoes], could they 
both hear two sonic booms at different times?  

If so...and a third observer was in the middle, between the two pressure 
gradients.......  Is it possible for two sonic booms to take place given 
off by the same plane and heard at the same time?  Would it be amplified, 
the same, or less than a common sonic boom?

To sum:
Plane exceeds sound barrier via a tail-wind.
Boom on ground-level or no?

Could odd conditions and a "perfect" locale entail a larger/lesser 
effect?  Resonance or dissonance?

Thanks.

Re: variations in sonic boom under perfect-unusual circumstances