I run tubes for TT/Tri (enve/turbo cotton) .. I'm running tubeless on my Groad bike currently and yes depending on tire/rim combo = PITA.. anything Enve/Schwalbe is PITA.. I dont know about Zipp... HED was cake.
I pretty much only do sprint/oly... and plan to stay with tubes.
I pretty much only do sprint/oly... and plan to stay with tubes.