Originally Posted by Psimet2001

Then you haven't done much tubeless then. As a shop owner I have run into piles of combinations that took some finesse even with a compressor that were absolutely impossible with a regular floor pump. One of the tubeless ones with a chamber can usually get the job done.

On the "why would anyone" bit... For the number of flats I have had with a tube (1 in the last 5 years or so) I have absolutely had to do way more for the tubeless systems I have ran than for any tube.