I have been tubeless for about six months now. So far it looks like one flat self-sealed. In terms of the work, most tires I found super easy to mount, but a few were near impossible to seal. So, if you are not a mechanical fiddler type like I am you might find it overly annoying/frustrating in some cases. For me, I enjoy a mechanical challenge and tubeless tires can be one! So it has been a lot of fun. In terms of riding there does seem to be a bit of benefit in terms of slightly less resistance and slightly lower pressures working. For my road kit I now just carry Stans Darts, a patch, and a pump. No spare tube unless I am riding in the middle of nowhere.