We know how fast the pendulum is swinging at any time $t$, call this velocity $v(t)$. As was stated in the problem, this can be assumed to be measured in rad/s although any other velocity works after a transformation. At the apogee of the swings, this velocity will obviously be $0$. The pendulum is also losing energy to friction between the fulcrum and whatever it is attached to. Crucially, the energy lost to friction can represented by $\Delta \theta K$ for some constant $K$ and positive change in pendulum angle $\Delta \theta$.
Now, to solve this problem we need two swings in total (not counting the initial swing where we don't know the starting point). For reference, call the first apogee $A$, the second $B$, and the third $C$. We can get the $\Delta \theta _{AB}$ with
$$\Delta \theta _{AB}=\int_{T_A}^{T_B}|v(t)|dt$$
where $T_{A}$ is the time when the pendulum is at $A$ and $T_B$ is the time when the pendulum is at $B$. In a similar manner
$$\Delta \theta _{BC}=\int_{T_B}^{T_C}|v(t)|dt$$
We can also find the arc length of $AB$ and $BC$ using $\Delta \theta l$ where $l$ is the pendulum length:
$$L_{AB}=\Delta \theta_{AB}l$$
$$L_{BC}=\Delta \theta_{BC}l$$
Next, we have to talk about the 'heights' of the pendulum at $A$, $B$, and $C$. What heights, you might ask since we are trying to find which direction down is? Well... it actually doesn't matter which direction down is initially since we only need a reference point.
For example, let point $P$ be the distance halfway in-between $B$ and $C$. Call this direction 'down'. We can calculate the change in 'heights' of the apogees by
$$\Delta z_{AB}=\left|l\cos\left(\pi \frac{L_{AB}-\frac{L_{BC}}{2}}{2\pi l}\right)-l\cos\left(\pi \frac{\frac{L_{BC}}{2}}{2\pi l}\right)\right|$$
Here
$$L_{AB}-\frac{L_{BC}}{2}$$
is the distance along the pendulum arc of $A$ to $P$ and $\frac{L_{BC}}{2}$ is the distance along the arc of $B$ to $P$. In a similar manner
$$\Delta z_{BC}=\left|l\cos\left(\pi \frac{\frac{L_{BC}}{2}}{2\pi l}\right)-l\cos\left(\pi \frac{\frac{L_{BC}}{2}}{2\pi l}\right)\right|$$
Of course, this is $0$ which follows since we chose the point in-between $B$ and $C$ as our reference point.
However, there was nothing special about choosing $P$ to be halfway in-between $B$ and $C$. Let $\phi(t)=t:[0,1]\to [0,L_{BC}]$ be the distance along the arc (starting $B$ and ending at $C$) between points $B$ and $C$ that we choose 'down'. Then the above equations (after simplifying) become
$$\Delta z_{AB}(t)=l\left|\cos\left( \frac{L_{AB}-tL_{BC}}{2 l}\right)-\cos\left( \frac{(1-t)L_{BC}}{2 l}\right)\right|$$
$$\Delta z_{BC}(t)=l\left|\cos\left( \frac{tL_{BC}}{2 l}\right)-\cos\left( \frac{(1-t)L_{BC}}{2 l}\right)\right|$$
Crucially, we now can vary what we call 'down' and get different changes in energy. These changes in energy must match the losses in energy from friction. That is
$$\Delta z_{AB}(t)mg=\Delta \theta _{AB}K$$
$$\Delta z_{BC}(t)mg=\Delta \theta _{BC}K$$
With these two equation, we can cancel $K$ and $mg$ to get
$$0=\frac{\Delta z_{BC}(t)}{\Delta \theta _{BC}}-\frac{\Delta z_{AB}(t)}{\Delta \theta _{AB}}$$
This equation can be numerically solved for the root $t_0$. As experimental inputs it requires $v(t)$, $T_A$, $T_B$, and $T_C$ (the $l$ parameter will actually drop out since the arc length is a constant times $l$). This $t_0$ is the percent distance from $B$ to $C$ that true 'down' lies.