I got stranded with a flat on tubeless because I couldn't figure out how to remove enough of the tire to insert a tube. Now that I understand what to do, I'm still nervous it'll happen again. As odd as it sounds, I don't notice much of a difference vs. clinchers.
Sometimes instead, I wish that I bought tubular wheels because I know for certain how to perform a roadside swap, and tubulars have a much more distinctive lightweight feel than tubeless.