I run tubeless on both on and off-road wheels.
Most of my road rides are 100+ miles with groups some comfortably running into 200+
Literally the only stops we’ve ever made have been for people using tubes. Several of us running tubeless have “punctured”, evidenced by sealant spray, and not had to so much as stop.
One ride the same guy had the misfortune to puncture five times in the same ride (tyre checked and cleared of debris each time, just mucky roads and misfortune) and each time we were digging further into bags to find a remaining tube.
We have, without a word of a lie, not had to stop a single time for a non-sealing/repairable tubeless puncture.
I will “sell” tubeless into anyone I can who plans on riding with us because its just been so much better for us, to the point of frustration when you’re all stood at the side of the road for a fifth ride of the year where it is the same person fixing a tube while the rest of you who have done massively more rides haven’t had to stop once.
Tubeless on MTB 6+ years, (because I was still on 26" till then, and a SLOW adopter; switched as soon as I bought a new Trek FuelEX carbon 29er, and have never regretted it.)
Same story when I finally bought a new roadbike summer of 2019, a '20 Trek Domane SLR, with 32mm tire width. Had it set up tubeless at the start and have never regretted that. I run about 46psi front, 51psi rear, and the only flat I had to deal with in over 20,000 miles was because I left the OrangeSeal too long without a refresh, and it dried out.
I did have a pinhole leak in the first 5 miles of a 100 mile day that sprayed sealant on the bike and the rider behind as it sealed itself up. We stopped and checked it, found it already sealed up, and didn’t even have to top up the air pressure at all.
I’ll admit to not having many flats ever on road rides anyway, so it’s not a common problem for me in this rural area. But I wouldn’t dare to run such low pressures with tubes, and the comfort and greater traction and control of 32mm tires vs previous 25mm is HUGE to me.
I’m DONE with “skinny” tires and tubes, except for emergency repairs.