I think you're mistaken about the $20K per show thing. Maybe in a major rock band, but unlikely for a hired gun. Regardless of the gross at a concert, the money is fronted by the label (loaned to the band) who has to pay it all back out of profits. The drummers are usually salaried, just like the sound guys.
Lots of talented name drummers are teaching, doing clinics, hustling, etc., for the money. Most of the guys you mention do van tours with their own fusion projects, not bus tours, because they don't make much (or lose money) and need to save money. The guys mentioned have done well because of all the Pop recording work they've done.
Remember, the old joke:
Q: How can you retire with a million dollars playing Jazz?
A: Start with two million.
Brad




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