I have to say...I had been a bit skeptical of tubeless until I set my first set up a month ago.
I put a set of Vittoria Terreno Dry 40mm tires on my stock, NON tubeless rims. Set up with one pump of my floor pump, and have not had even a single burp, even when running 19psi (too low, was testing..) into hard corners during CX practice, and completely folding the tire over multiple times.
I credit skinnystrippers, which @
chas58 turned me on to. At 19psi, the tire is soft enough I can manually unseat the tire bead with my thumbs(quite easily I might add...), and I still lose no pressure. For $10 and 10 grams, I'd say they're a no brainer for anybody running tubeless in any scenario.