Tubeless tyres

Tubeless tyres are pretty expensive - you can usually get a pair (try Just Riding Along) for around £80. But don't expect less hassle getting them fitted - the beads are very stiff so they need a fair amount if force to get them on. Then there's the fun of getting them to seal! I've had some that seated and sealed immediately using just a track pump, and others that it took literally hours of serious effort and a bunch of CO2 canisters...

Once on, they're excellent though. I'd strongly recommend sealant (based only on my personal experience) - one of the big advantages of tubeless is the self sealing for many punctures! I have used stan's sealant and Caffe Latex, and found the latter to be brilliant. Needs topping up every so often, and it does run out if you have a few punctures in quick succession, but it sealed all sorts of holes in my tires (up to about a 1.5cm long cut). If you do get a puncture that won't seal, just pop in an inner tube to get you home and repair the tyre there (there are kits available). The tyres are an even tighter fit with a tube, but it's doable on the road (and won't be any more difficult than the gatorskin, I wouldn't think).

The ride on tubeless is nice too - the ability to run at lower pressures gives a lovely smoothness, and helps with grip in the winter too.

I short, going tubeless might well reduce the number of punctures that leave you changing a tube by the side of the road - but probably won't reduce your hassle much when you do have to stop. Whether the cost (and potential fiddliness fitting them) is worth that and the nice ride quality is up to you! I have to confess, I've moved back to standard clinchers for the moment on cost grounds, but I'm still tempted to go back...