Two thoughts....
1) my LBS mechanics scream at me every time I suggest that I want to go tubeless on my roadbikes.... as far as they are concerned, no worth the headaches for road (but most definitely worth it for mountain bikes)
2) I usually use Michelin Pro4s on my bikes.... they are an absolute ***** to pull over the rim lips. In my garage (and I do throw it in my jersey pocket if my wife isn't available for road side pick up) I use a Kool Stop bead jack (google it...use the vendor link of your choice...). Absolute miracle gadget for tough tires. When I burn out my supply of Michelin's I'll probably just to stick to Conti GP4k/5k in the future just because they do mount so much easier....