>>1678446the initial setup is easy if you have rims designed for tubeless, otherwise it can be annoying or easy depending on luck. regular maintenance isn't really needed other than occasionally checking sealant levels through the valve and topping up as needed. the hassle is when there's a puncture that the sealant won't heal without intervention. maybe you need to use a worm or a dart or equivalent, and you have to do it right or you could puncture the rim tape or the worm will pull itself out (especially if it's not fresh). maybe you need to actually remove the tire and install a tube to get home. you're dealing with latex sprayed all over your frame and probably your legs
this tends to happen the most towards the end of the tire's useful service life, similarly to how a regular clincher tire also gets more punctures towards the end of its useful service life
you also need to be a little more careful about matching tires to rims because there's a theoretical risk of the tire bead just blowing off your rim altogether since there's no tube to maintain integrity when there's a fit problem. this is rare and it mostly happens to people who are being retards like putting a tire that's 1 or 2 sizes beyond the ETRTO recommendations and also running pressure beyond the tubeless pressure recommended by the manufacturer, but the narrow tolerances for tubeless on smaller tire/rim widths means there's more room for mistakes, manufacturing defects, or simple user negligence to become an actual issue
also the sealant can eventually dry up inside the tire, this mostly a problem if you live somewhere dry and you don't ride your bike regularly. if that happens the puck of dry sealant can interfere with the free movement of liquid sealant even after you top up, so leaks don't get an instant bath of liquid sealant, and you have more spraying before the hole is plugged