Removing the headphone jack doesn't push wireless into the mass market. It was already in the mass market and it was going to be in the mass market regardless of how Apple designed their phones. If you want to use a wireless headset, you always could. Removing the headphone jack didn't give you any sort of advantages as a wireless user, it just removed an option you didn't use.
And no, it's not courageous to do something dumb and getting skewered for being dumb is not evidence of courage.
It has increased the speed of wireless headphones uptake.
You can call it dumb all you like, but whether something is dumb or not is completely separate from whether it is courageous or not.
I'm amazed by people hating something so much that therefore, in their minds, makes it impossible to have other qualities that might have a positive connotation.
And no, it's not courageous to do something dumb and getting skewered for being dumb is not evidence of courage.