Background
Let $\mathcal{A}=(Q,\Sigma,\delta,q_0,F)$ be a minimal DFA for a regular language $L$ such that $|Q|=n$, and let $\equiv_L$ be the relation given by $$x\equiv_Ly\text{ iff for all $u$: }xu\in L\Leftrightarrow yu\in L.$$ It is known we can identify the states of $\mathcal{A}$ with the elements of the quotient $\Sigma^*/\equiv_L$. Moreover, since $\equiv_L$ can be characterized by $$x\equiv_Ly\text{ iff }\hat\delta(q_0,x)=\hat\delta(q_0,y),$$ we know we can choose elements $w_1,\ldots,w_n\in\Sigma^*$ such that $$Q=\big\{[w_i]_{\equiv_L}: i\in\{1,\ldots,n\}\big\},$$ and $|w_i|\leq n$ for all $i$, that is, we can choose representatives for $\Sigma^*/\equiv_L$ of length at most $n$.
This is useful because, given the minimal DFA $\mathcal{A}$ (whose states might be given in an abstract way, not necessarily with elements of $\Sigma^*/\equiv_L$), we can obtain a set of representatives of $\Sigma^*/\equiv_L$ by running $\mathcal{A}$ with all inputs of length at most $n$ and marking the states that have already been reached with a flag. Whenever an unmarked state is reached with a string $w$, we flag the state and add $w$ to the list of representatives. This might not be the most elegant or efficient algorithm, but thanks to the upper bound we can be sure it finished and it computes what we want.
Question
Is there a general method of estimating a minimal length of representatives of an equivalence relation? I'm assuming, of course, that the universe consists of elements of finite length (e.g. $\Sigma^*$).
In particular, I'm looking for a similar upper bound for the relation $\sim_L$ given by $$x\sim_Ly\text{ iff for all $u,v$: }uxv\in L\Leftrightarrow uyv\in L,$$ which can be characterized by $$x\sim_Ly\text{ iff for all $q\in Q$: }\hat\delta(q,x)=\hat\delta(q,y),$$ where the automaton is minimal.
Thanks in advance for your guidance.
Update: to be a bit more precise, what I want is an upper bound $M$ for the smallest representative of a class, so I can do an algorithm of the form: ``check all the words of length at most $M$...'' and be sure that all classes are covered by some representative at least once.