If you're primarily after a more supple ride and lower pressures, the first thing I'd do is lower your pressure - you're running a little high for 28s and your weight, IMO. Start there, then reassess.
As far tubeless, I think that it's a great solution if you get a fair number of flats. If I didn't need the benefit of flat protection, though, I don't think that I'd take on the extra maintenance just to lower pressure a handful of PSI.