I went to tubeless on our current tandem after started having frequent flats with tubes. In hindsight, I think it was from running tires that were too lightweight - Panaracer Pacenti Pari-Moto. I turned them tubeless and still got flats - but with the tubeless setup I was often able to get them to seal up by putting the puncture at the puddle of sealant in the tire. Now I've switched to the Specialized Sawtooth 38 mm tubeless and all is well. And I run Skinny Strippers on all my tubeless setups which makes getting inflated a breeze.