this is a followup/ sequel to this recent question which was answered, this one presumably significantly harder. consider a deterministic FSM transducer $F$ and its mapping $F(x)$ of an input word $x$. define a sequence/ composition of such mappings $x_n = F(\ldots F(x_1))$ where $F^n(x)$ is $n$ sequential mappings of $x$. the sequence terminates if/ "at the point" that $F(x_n)$ is unaccepted (by the FSM transducer).
now consider/ define a property of such sequences "descending". a FSM sequence $x_i$ is "descending" iff $|x_i| \geq |x_{i + 1}|$ where $|x|$ denotes word length, and for all $i,j$, $x_i \neq x_j$. (by defn all such sequences must be finite/ terminating.)
question: given an input regular language $L$ and a FSM transducer $F$. is it decidable if all sequences $x_n = F^n(x) = F(\ldots F(x))$ for all $x \in L$ are descending?
a complete answer would be ideal but prefer partial answer(s) to none at all. looking for nontrivial analysis, reduction(s) to known problems, refs to related literature etc.
motivation/ background: a long story, but inspired/ related to investigation of a highly studied open number theory problem. the basic idea is to look for/ formulate a generalized loop invariant function applicable to automated theorem proving.