I've toured tubeless for a short time in Costa Rica on a mix or road and gravel(some of it quite big chunky gravel). I've commuted and done bike delivery tubeless for thousands of miles. This was all done on Stan's tubeless rims, Stan's sealant, Gorilla tape rim strips, valve stems cut out of old tubes, and regular tires. I was kind of surprised to find that I also didn't end up having to take my tires to somewhere with an air compressor. They seated with my regular bike floor pump. A couple fast strokes got them to puff out and push against the rim. After that I just pumped up the tires as usual and they slowly seated. It did take a good bit of pressure to get that final pop to full seating on the rim. And it was a bit of a loud pop, so I'd recommend not doing that indoors or using earplugs. I have to say my experience has been fantastic. I've only gotten one flat on my tubeless set-up. That was on a mountain biking trip where I was running too low of pressure and hammered too hard through a sharp volcanic rock garden. Snake bite. I threw in a tube and continued my trip(getting one more flat on the tubed tire before the end). Totally my fault for running low pressure and riding too aggressively on that terrain.
Other than that, I've completely worn out two pairs of new tires without ever getting a flat in thousands of miles. One set of MTB tires and a set of commuter tires. The one tire was practically a slick down the center before I changed it out, still no flats. I think I would have been getting flats if I had run a tubed tire to that level of thin tread. I'll Always carry a spare tube on tour, but I'll also always go tubeless from here on. And all of this is not even mentioning the superior ride quality.
I will say I don't understand the more modern road tubeless set-ups that have a thicker tubeless ready tire and don't use a good sealant. That just seems like the worst of everything. Heavy, thick tires, no good sealant to stop a puncture if you do get one, and high pressure required to seat the bead. What a disaster waiting to happen...