What’s challenging is I guess you can’t know a priori much about the actual genetics at play so at a certain point it becomes hard to know what’s simply phenotypic variance independent of genetics and what’s actually genes - it could take quite a while to be certain you’ve “converged”. Or for something more subjective/without an obvious strong genetic link, it could take a while to rule out the possibility of breeding for the trait at all.
Like for humans, I’m highly confident you could do some basic process over 10 generations to breed some ridiculously tall people. But it helps we know it has huge variance, is highly heritable, is easy to measure, and is polygenic. Probably a lot harder to try to breed “nice” people or people with thick skin. The fact dog breeders can do things like that is much more impressive IMO.