I can relate to Titus' conundrum as I have found myself pondering the exact same scenario many times. Great article but it suffers big time from selection bias. Of course all the successful proprietors are going to say go with your passion. I'm sure you could find many times more who followed their hearts only to lose their financial stability, home, future, etc and end up with nothing but an experience. That's not to say don't do it, just realize there are serious consequences of failure.
You do realize you can pinch flat tubeless? The top enduro guys are pinch flatting with DH casings and cush core! I've had my share of pinch flats when I drop the pressure too much with single ply tires.
I've been running the FlashFlo for 2 years now. It preceded the Palos and was intended for hiking. It's not as voluminous as the current crop but I made one modification to the hose routing I recommend for anyone considering going fanny style:
I too was concerned with catching the hose on the seat and not being able to sip easily from a waist mounted hose. Instead I cut a small hole in the top center of the pack and route the hose up the center of my back and over my shoulder (ala backpack style). The Flash Flo came with a small hose clip you open/pinch to whatever shirt/jersey you're wearing. The hose was just long enough to do this. I can sip as easily and regularly as with backpack/hydration and the hose never gets hung up.