Wow. I'm a bit late getting into this, but here's my take on this:
1 - The only thing that really matters in photography is your optics and whether you understand how to use them(hint, if you have only 2-3 lenses, you're making massive compromises already unless you're doing only one type of shooting, like large format scenery)
If you go to his site, he goes on and on and ON about gear and lenses and so on.
He may say it doesn't matter, but over and over on various sites in addition to his, one thing is always mentioned the most. The lens.
So it should be changed to "The most important piece of equipment in photography is the lens." This I can agree with, and it's why a lot of old school cameras from the past still do amazing things. It's hard to beat a 40 year old 50mm 1.2 lens for low light with most of the newer stuff. At best they tend to equal it. Yet, that old pre-digital/non AF lens can be had for dirt cheap in a lot of cases.
2 - Optical always will trump digital when it counts. No place is this more apparent than in the prints and enlargements. Typical 400DPI printing looks fine because it's what we're mostly used to, but if you find a good professionally done old-school enlargement and put them side by side, it's kind of sobering. We forgot what good printing looked like thanks to the labs and computers cutting corners.
That said, a lot of good results can be had for cheap with good old fashioned film and a good manual lens that you can't get with digital unless you spend literally 10x the price. A lot of the examples that I see Ken and others tout as reasons why the gear isn't important are shot with old cameras with good optics and good film. This gives you a huge advantage versus digital right away, especially at the lower end, and most of them are dead-simple to use.
IE - A $50 used rangefinder with some modern film blows the socks off of a typical $500 digital camera. That's not the gear not mattering, it's in fact, exactly the opposite. The thing Ken and the others miss is that just because it's less expensive doesn't mean it's not worthy compared to the new toys.