W/R/T the advantages of tubeless:
- Fewer flats: I think you know where I stand here. I've had two flats this year and half of those have been tubeless flats. I've seen more folks get flats with tubes, it's true, but I've seen a few get flats with tubeless as well and given the ratio of tubes/no-tubes, well you get the picture. I don't see much difference (yet)
- Run lower tire pressure without pinching: Without a tube to pinch I suppose this is self evident, but tubeless are subject to "burping" which is basically the same thing in my mind ie., if you run your pressure too low you risk getting a flat. Also, perhaps you won't pinch or burp, but if you are in a position where that was a possibility then you certainly risk damaging your rim. It looks to me like a wash here.
- Better ride quality: I haven't noticed poor ride quality with tubes, but I will have to wait for some singletrack time with the new setup to figure that out.