Regular antichain subset of the iteration of a regular language

This problem comes from a typing problem (non structural subtype assignment). Given a regular language R, does there exist a regular language U such that: U is an antichain for the prefix ordering $\forall u \in U, \exists r \in R, r < u < r^\omega$ $\exists u \in U, r \in R, r < u < r^\omega \wedge |r^{-1}u| > ||U||$ where $||U||$ is the number of states of the minimal automaton recognizing $U$, and $r^\omega$ is the infinite iteration of $r$. I conjecture that such language does not exist, though I don't find an approach to attack it. If such a language does exist, it would be interesting to know if there can be an infinite number of words such that the third point holds or not.