If $\mathcal M$ is a model category and I know that $A$ and $B$ are isomorphic in $\mathrm{Ho}(\mathcal M)$, is it guaranteed that there is a zigzag of weakequivalences in $\mathcal M$ connecting $A$ and $B$?
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Yes. The isomorphism in $\mathrm{Ho}(\mathcal{M})$ is represented by a morphism in $\mathcal{M}$ from a cofibrant replacement for $A$ to a fibrant replacement for $B$. The "converse to the Whitehead lemma" states that a map in a model category is a weak equivalence iff its image in the homotopy category is an isomorphism. Combining this with the definition of (co)fibrant replacement, we see that $A$ and $B$ are connected by a 3step zigzag of weak equivalences. 

