My primary reason for going tubeless is that the folks I know that have done it report that they have gone "years without a flat".
I get a flat at least once a month.

I'm a B+ rider trying to move up to A.
But the primary reason for riding is the cardio and enjoyment of the outdoors.

Changing a tube at the roadside during the warm months is not such a big deal. But when it gets cold I hate hate hate changing a tube. Cold fingers and the inevitable chill would make me consider tubeless.

I might even consider two sets of wheels - tubeless alloy rims for cold weather / winter riding and clincher carbon wheels for warmer weather.

Gonna discuss with my LBS in the coming days. If rheir response is "Oh yeah you should go tubeless we've done lots of conversions" then I am in. If they hesitate or discourage then I will need to consider further....

Further comment and discussion on this topic is welcome.