The question for the first example you gave where the tubeless tire went flat, didn't self seal and had to be "tubed" is, did that person have a tubeless tire puncture kit which would include at least 2 and as many as 4 items (plugs, a temporary leak stopper, a small bottle of sealant, and a pump or CO2 (CO2 used in a "special" way)) ? Probably not. And, if not, that simply confirms my supposition that many of the problems seen are due to the rider not being equipped and/or trained for a a relatively speedy recovery. The other question concerns whether the rider periodically maintained the sealant, another possible issue that makes a speedy recovery more problematic.
Note, I'm not pushing tubeless but, rather, am trying to inform the club about its possibilities. For me the jury is still out when it comes to high pressure (above 80 lbs) tires though I believe that a superior plug kit (the "Stan's Dart" kit for instance) can handle them well, and quickly. I think that tubeless will become increasingly popular because of its advantages, especially as the technology improves along with the know how concerning how to handle punctures.