I'm ambivalent about road tubeless. I've got two wheelsets set up with tubeless - Ultegra 6800 wheels with IRC Roadlite tires, and Hed Ardennes Plus wheels with S-Works Turbo tubeless. I've had zero issues with the first. The presta nut came off in the pump head on the second; when I pulled the valve core to replace it, one side of the bead came unstuck and it was harder to re-seat the tire than it was to originally seat it. That may have something to do with the fact that I had Stan's in the tire and it was a lot slicker. As far as holding air, both sets are about the same as clinchers with tubes.

I'm with [MENTION=99188]tetonrider[/MENTION] in that I don't find the ride quality to be noticeably better than good clinchers with tubes and I don't get but 1-2 flats/year. The additional hassle of mounting them and the additional cost outweigh the advantages for me.