I'm going to do my south-north ride tubeless. Right now I have a Hutchinson Intensive on the rear with over 2600 miles on it and it's still going strong. There are 2 spots that I can tell have been sealed, but I didn't notice either one while riding. I ride in an area with a lot of thorns. No flats at all on this tire. It's not a cheap tire, but there are always deals if you're patient.

I don't have any real worries about going tubeless on the ride. I'm going to take 2 spare tubes and a patch kit with me (which I would have done on a standard setup anyway) in case **** hits the fan. That happened to me once on my old Fusion 5s (garbage tires, BTW) and it really wasn't as messy as I was expecting it to be.

I ride tubeless mainly for the protection against thorns. The ability to run lower tire pressure is a nice side benefit. I don't ride anything super low around here because the roads are pretty good, but you never know what you're going to run into on a tour. If the roads are **** or you run into a lot of rain it's nice to have the option to go low on the tire pressure.