Last winter, I went tubeless with Continental 5000 tires on Reynolds carbon wheels. They were the toughest tire I have ever mounted. I had to take it to the bike shop and the bike shop took 4 hours and invented new curse words. I had orange seal in both tires. They worked great when they worked. I had constant valve leak and I knew if I got a flat, I would have to make the call of shame.
I took my wheels to the lbs and they replaced the valves. A week later, I had the same leaky valve problem. I finally gave up and went back to tubes.