So you're just after the ride quality? What tires/tubes are you currently using? Going to a more supple combination might be the easiest way to get what you're looking for (or close enough), if that's the main thing that you're looking for.
I'm a big proponent of tubeless, but recognize that it's not for everybody. For me, the primary appeal of tubeless is that of flat protection and ride quality is a really nice bonus. There's no free lunch, though - it's a trade-off of work. Mounting and seating tires can sometimes be difficult (though, after a few years of practice, it's become trivial) and sealant means that there's more cleanup involved when you replace tires. In exchange, it's exceptionally rare that I'll have to address a flat on the side of the road.
If that sounds like a fair trade-off, are you willing to learn a new skill set, going through a potentially frustrating learning curve? Are you willing to add sealant level checks, every 6-8 weeks, to your maintenance regimen? If so, yeah, I'd strongly consider making the jump. If not, stick with tubes.