I have never ridden tubeless tires, so keep that in mind.
I have two training partners that ride them and they have had more flats than I have, almost twice as many. Both of them use the "stans" tubeless tires (sealant) and nearly every time, the sealant fails to stop the leak. They always carry spare tubes (two, one for each tire) and have had to spend a fare amount on new tires due to flats...
In my opinion, the performance gains are NOT worth the extra hassle.
-TB