I’ve been riding the Zipp 303s and tubeless for about a year and a half now; roughly 5000 mi. I’m 185lbs and running pressures at 62/65 F/R. The wheels have been solid for me using the SWorks Turbo RapidAir and Schwalbe Pro One TLE tires; both mounted easily with a track pump. Orange Seal Regular has been the sealant of choice. I have opened up the freewheel to clean and service twice since owning them.
Talking about road tubeless in general, in the two years I’ve been tubeless, I had 1 real flat and it was about a month ago with the Schwalbe’s in the rear. I took a nail to the sidewall, so I stuck a butyl tube in it and rode on. That tire was patched but I took another nail in the tread 2 weeks ago. This time I didn’t notice it while out for a century; it wasn’t till the following day that I noticed while cleaning the bike. It sealed and held up for who knows how long.