been tubeless on the mtb for years, never going back. I'm sure I'm jinxing myself here, but I haven't had to walk home, add a tube, whatever, in over 4 years of weekly riding. Once, the sealant was pretty dry and wasn't sealing completely, but I was still able to ride home on a tire with about 15psi.
I just switched to tubeless for my road/gravel bike (sold the roadie). It's only been about 3 months of mixed terrain riding, but just Saturday, tubeless likely saved my ride. I had a puncture in the thread of the tire, and within about 100 yards, it was sealed, and I was good to go. I probably still had 40-50psi, so I didn't even mess with my spare CO2. I just finished out my ride, which was about 20 more miles. I will say, it was a damn mess on the bike and my back side as the sealant sprayed from the spinning tire.
I would totally make the switch to the TT bike if the wheels I use were tubeless ready. Although, I do use latex and sealant, so I'm only giving up a little weight and marginal RR.
I always keep a spare co2 and tube, plus now I carry the little plugs for larger punctures. Tom A. has talked a lot about options here.
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TEAM F3 Undurance