My first attempt at Tubeless wheels was with Continental GP5000's. I about broke my hands trying to get them on. I took it to the bike shop and it took them 4 hours and the invention of new swear words. There was no way I could fix a flat with them on the side of the road so I went back to tubes.
My second attempt at tubless was with Micheline Power Road 28's. I warmed them up with a hairdryer, and they went on with just a little strain. They beeded on the first attempt and I've got 1200 miles on them without a problem. They ride smooth and feel fast, I will definitely buy these tires next time I need tires.