An analysis of Claim 1:
For fixed $q\ge e^{-1}$, let use denote $p$ by $x$ and define these functions:
$$f(x)=\left(1-q\right)^{2}\log\left(\frac{1}{x}\right)-q^2\log\left(\frac{1}{q}\right)$$
a decreasing concave function with the only root $r_f=e^{\frac{q^2\log q}{\left(1-q\right)^{2}}};$
$$g(x)=\max\left(q,0.5\right)\left(1-\max\left(q,0.5\right)\right)\left(\log\left(\frac{1}{x}\right)-\log\left(\frac{1}{q}\right)\right)-\left(q-x\right)\left(x\log\left(\frac{1}{x}\right)+q\log\left(\frac{1}{q}\right)+\left(1-x-q\right)\log\left(\frac{1}{1-x-q}\right)\right)$$
a function with maximum two roots (it follows from that $\frac{g(x)}{q-x}$ is a convex function): the smallest $r_g$ and largest roots $R_g$ which may not exist for all values of $q$, in that case we use $+\infty$ ($R_g=q$ for $q \ge 0.5$ and $R_g=+\infty$ otherwise; moreover, as I checked $r_g$ exists even for $q=1-10^{-10}$ by observing that $\small g\left (\frac{1-q}{2} \right )<0$);
$$h(x)=x\log\left(\frac{1}{x}\right)-q\log\left(\frac{1}{q}\right),$$
a concave function with the smallest root $r_h=e^{W_{-1}(q\log q)}$ and largest root $R_h=e^{W_{0}(q\log q)}=q$, where $W_{0}$ and $W_{-1}$ denote two branches of the Lambert $W$ function (as $e^{-1} \le q\log q<0$, the equation $x^x=q^q$ has two real solutions).
The above functions can be seen visually here, which also shows how the claim holds for any $q\ge e^{-1}$. You can see that the red area (where none of (∗) and (∗∗) holds) and green area (where all initial conditions of the claim hold) have no overlap.
Now we can derive the following equivalent condition for Claim 1:
Claim 1 is equivalent to show $$\min (r_f, r_g) < r_h \tag{1}$$ for any $q\ge e^{-1}.$
As we have $f(r_h)<0$ for $q>q_2 \approx 0.7307$ where for $q=q_2$ $r_f=r_h$, to prove (1) it remains to show
For any $e^{-1} \le q <q_2 $ $$g(r_h)<0 \tag{2}$$ where $r_h=e^{W_{-1}(q\log q)}=\frac{q\log q}{W_{-1}(q\log q)}$ and $q_2 \approx 0.7307 $ satisfies $$(1 - q_2)^2 = q_2\exp \left ((q_2^2\log q_2)\left(1-q_2\right)^{-2} \right ).$$
Note that for $e^{-1}<q< 0.5$, we have two intervals $(0, r_g)$ and $(R_g=q, r_f)$ on which none of (∗) and (∗∗) holds, but assessing the second one is not required as it clearly appears after the interval $[r_h,R_h=q]$, over which the initial conditions of the claim are satisfied.
It is worth mentioning that $\min (r_f, r_g)=r_g$ iff $q\le q_0 \approx 0.773$. In fact, for $q\le q_1\approx 0.916$, $r_g < r_h$, so we need (∗∗) only for $q> q_1$. Another observation is that $a=\frac14$ in (∗) works for all values of $q\ge e^{-1}$ excepting a very short interval that includes $(0.72,0.73)$.
Proving (2) seems difficult as $r_h$ is a highly complex quantity. However, for $r_h$ we have the following lower and upper bounds [2]:
$$\small r^L_h=\frac{q\ln q}{-1-\sqrt{2\left(-\ln\left(-q\ln q\right)-1\right)}-\left(-\ln\left(-q\ln q\right)-1\right)}$$
$$\small r^U_h=\frac{q\ln q}{-1-\sqrt{2\left(-\ln\left(-q\ln q\right)-1\right)}-\frac{2}{3}\left(-\ln\left(-q\ln q\right)-1\right)}.$$
Hence, instead of proving (2), to make sure that $r_g$ is smaller than $r_h$, we can prove the following sufficient condition:
To prove Claim 1, it suffices to show $$g(r^L_h)<0 \tag{3} $$ for $e^{-1} \le q <q_2 .$
The function $$\frac{g(r^L_h)}{q-r^L_h}$$ is depicted below (source) for $0<q<1$
$\hspace{3cm}$
This figure clearly shows $g(r^L_h)<0$ for $e^{-1} \le q <q_2$, where the boundaries are displayed by vertical lines. Considering that the values of function $\frac{g(r^L_h)}{q-r^L_h}$ is sufficiently smaller than $0$ in the range of interest $e^{-1} \le q <q_2$, this observation can be straightforwardly converted to a rigorous proof using interval arithmetic, which is a usual practice in such a case. Thus, (3) holds, and this implies (2) and (1), which are equivalent conditions for Claim 1, and we are done. $\tag*{$\blacksquare$}$