I have had 2 experiences with tubless. Setting up tubeless on a TLR rim with tubeless specific tires and stans worked great, no mess, short set up time. My attempts at "ghetto tubeless" with gorilla tape, a standard rim, and stardard tires resulted in an hour of sweating, swearing, and trying to wipe a bunch of stans goo from my garage floor....couldn't get the bead to seat. I may give it another go with a different set of tires (wire bead), if that does not work, I'm gone with the "ghetto" method.
As far as the benefits of tubeless, I can definately notice more traction, a more supple ride, and like the lower psi. However, it wasn't some great zen like experience that some people make it out to me, IMHO. Then again, I usually dont get a ton o flats anyhow.