III Corp,
You make some valid points but I would also like to fill in the cracks. Boeing has been correct in assesing market conditions and aircraft for a few decades also. First let's look at them bowing out of the SST program after realizing that the fuel guzzling supersonic jet would not have enough seats to justify it's building. After the Russians became the first to launch a supersonic jet the concorde followed. The concorde did not become successful until the very late nineties early 2000 when they were leased out for to charter operators who had pax willing to spend to be on the "Concorde." I would venture a guess and say that had the concorde accident not put that aircraft to bed a few years ago, the fuel prices today would have.
Next came Boeings decision to launch the B747. This was indirectly part of the reason for Airbus' launching a large twin, they then would be competing against the DC-10 and L1011 which came after the design of the B747.
We'll have to see who was smarter in the Airbus/787 design launch. Although they are not similar, the 787 is banking on the A380 to become a niche player and not be as hugely successful as the Airbus people think. The 787 will be going back to original route structure called O & D which stand for origin and destination. Remember back in the day ( well at least for those of you over 40) you could get on a plane and go to your destination without travelling through a hub? Boeing is betting big time that the population shifts around the world support this, coupled with it's reduced costs to operate through newer technology I think they have a good idea. While offering a beefier 747 to placate airlines until the 787 pans out. So far only one operator is interested in the 747-I and that's the same company that had a major influence on the development of the 737, Lufthansa.
Only time will tell.