Let $\psi:[0,1] \to \mathbb{R}$ be a concave, smooth, strictly increasing function satisfying $\psi(0) = 0$, $\psi(1) = 1$ and $\psi'(0)>1$. Assume further that $\psi$ is linear in a neighbourhood of zero, and set $c = 2\psi'(0)$.
Note that the assumptions $\psi'(0)>1,\psi(1)=1$ imply that $\psi$ cannot be linear up to $r=1$-it must become strictly concave at some point.
Set $t_0=\sup\{ \psi'(r)+\frac{\psi(r)}{r}=c\}$.
Question: Is $f(r)=\sqrt{c^2-(\psi'(r)+\frac{\psi(r)}{r})^2}$ infinitely differentiable at $t_0$?
As I explain below, $f(r)=0$ for every $r\le t_0$. So, this is equivalent to asking whether all the right the derivatives of $f(r)$ exist and are equal to zero at $t_0$.
Here are the details:
First, we note that the function $g(r)= \psi'(r)+\frac{\psi(r)}{r}$ is non-increasing, due to the concavity of $\psi$ (see a proof at the end).
Also, $\lim_{r \to 0}g(r)=2\psi'(0)=c$. These facts implies that $g(r) \le c $ for every $r>0$, and that $g(r)=c$ on $[0,t_0]$. Equivalently, $\psi|_{[0,t_0]}$ is the solution to the ODE $y(r)'+y(r)/r=c$ which implies that $\psi(r)$ is linear on $[0,t_0]$.
The fact that $g(r)$ is non-increasing implies that $g(r)<c$ for every $r>t_0$.
As explained in this partial answer, the smoothness of $\psi$ implies that $$\sqrt{c^2 - \left(\psi'(t_0+h) + \frac{\psi(t_0+h)}{t_0+h}\right)^2} = o(h^n),$$ for any $n>1$. However, unfortunately, this fact alone does not imply that this creature is smooth at $t=t_0$.
A proof that $g(r)$ is non-increasing:
$$ g'(r)=\psi''(r)+\frac{1}{r}(\psi'(r)-\frac{\psi(r)}{r}), $$ and both summands are non-positive. $\psi'' \le 0$ by concavity. Since $\psi(r)=\int_0^r \psi'(t)dt \ge \int_0^r \psi'(r)dt=r\psi'(r)$, the second summand is also non-positive.