The sealant should be checked occasionally, since it'll slowly dry out. The tires should (famous last words) hold air consistently. You may have heard about the difference between theory and reality...? 'Nuf said on that.

Personally, I'm not sold on road tubeless. If I lived where there were a serious goathead thorn issue, then maybe. Other than that, from a weight perspective it appears to be a wash, at best. But if you're getting TLR wheels, you can always try it out and see what you think.