What the book demonstrates
In No-Nonsense Classical Mechanics, the author spends some time discussing how point transformations in configuration space correspond with canonical transformations in phase space:
Specifically, the author demonstrates via this proof that a point transformation $q \mapsto Q = Q(q)$ implies that $p \mapsto P = \frac{\partial q}{\partial Q} p$.
How is this not a counter-example?
I don't doubt the proof, but I'm having trouble understanding this intuitively. For example, let us suppose we're in the context of a falling ball, where we can demonstrate via the Lagrangian that $p = m \dot{q}$. It seems to me that if $\dot{q} \mapsto \frac{\partial Q}{\partial q} \dot{q}$, then $p = m \dot{q}$ will then get mapped to
$$ P = m \left( \frac{\partial Q}{\partial q} \dot{q} \right) = \frac{\partial Q}{\partial q} \left( m \dot{q} \right) = \frac{\partial Q}{\partial q} p $$
and of course this contradicts the idea that $p \mapsto P = \frac{\partial q}{\partial Q} p$. What is wrong with my reasoning?