I had a tape leak at a recent event; didn’t even realized it until I had finished. Luckily, the leak sealed and the pressure remained at around 40psi. I checked the tire and found no punctures, and then realized the tape had failed at one point and the sealant made its way into the rim and out around the valve core. I re-taped both rims and have done a couple of rides since and no issues.
IMO, it’s very important to find a wheel/tire combination that works well together. I recently posted about my failed attempt to convert a set of Ultegra 6800 TLR to tubeless with GP5K TL tires and could never mount them. I wouldn’t want to be stuck out on the road with tires that I couldn’t pop the bead and remove in order to install a tube if needed. All of my tubeless tires are Mavic Yksion Pros, which some people have reported don’t last long, but they meet my needs because they install nicely on Mavic and Ultegra rims and roll very nice.
So far tubeless has been a positive experience for me. I’ve discovered about 3 punctures at home after rides that have sealed properly. I prefer to do repair work at home but it’s nice to know that should something happen that would require me to pop in a tube to get me home I can.