I resisted tubeless for about 5 years and flatting 6-8 times a year. After a particularly bad period of several flats in a short time, I took the plunge. My wheels were tubeless ready so it was just a matter of getting the tires, valves, and sealant. Was a bit of a hassle to set the bead on the first try but i don't expect that to be much trouble going forward. I know from finding sealant on my seatpost, that I have prevented at least one roadside repair so far.
Just to be clear, I would not bother with tubeless if I was getting 1-2 flats a year or less.