The value of an infinite series is defined to be the limit of the values of its partial sums:
$$ \sum_{n=0}^\infty f(n) = \lim_{N \rightarrow \infty} \sum_{n=0}^N f(n) \text{.} $$
so the right thing to do when trying to understand the convergence of the given series and its termwise derivative is to look at what the partial sums do as we add more and more terms.
Let's do that. Let's pick $a = 1/2$ and $b = 13$ (the smallest odd integer that satisfies $ab > 1 + \frac{3}{2}\pi$). (Aside: the image in your question has $a = 1/2$, $b = 3$, so is a picture of a much too tame function.) Let's define
$$ W_N = \sum_{n=0}^N (1/2)^n \cos( 13^n \pi x) \text{,} $$
the sum of the first $N$ terms. Also, since $W_N$ is a finite sum, we can find its derivative by differentiating term-by-term. (This doesn't always work for infinite sums because the (outside) limit for the derivative and the (inside) limit for the sum don't necessarily commute -- swapping the order of the limits can give different results. So more care must be taken when that happens.)
$$ W_N' = -\sum_{n=0}^N (1/2)^n 13^n \pi \sin(13^n \pi x) $$
Before we go to pictures, let's take a second to see what is already present. In $W_N$, the coefficient of the trig function is $(1/2)^n$. Since $0 < a < 1$, successive powers of $a$ get smaller -- successive cosines mix in with smaller and smaller amplitudes. Every time we increment $N$, the new term is dwarfed by each preceding term, so it's plausible that the function given by the sequence of partial sums settles into some limit function by making smaller and smaller adjustments as we add more terms.
However, the coefficients of the sines in $W_N'$, $(13/2)^n\pi $, are increasing faster than the powers of $\left(1 + \frac{3}{2}\pi\right) = 5.7123{\dots}$. This means each new sinusoid has amplitude at least 5-times larger (in fact, $13/2$-times larger) than the preceding one -- every time we increment $N$, the new term dwarfs the sum of all the preceding terms. This means the $W_N'$ do not settle in towards some function; instead oscillating with rapidly greater amplitude and frequency, failing to settle toward a limit.
Here's $W_5(x)$ on $[-3/2,3/2]$ and then on $[0,1/25\,000]$ (to show the contribution from the last term).
![W_5(x) on [-3/2,3/2]](https://i.stack.imgur.com/95LCE.png)
![W_5(x) on [0,1/25000]](https://i.stack.imgur.com/DKfXY.png)
Now let's look at $W_5'$ on the same intervals.
![W_5'(x) on [-3/2,3/2]](https://i.stack.imgur.com/uC5kF.png)
![W_5'(x) on [0,1/25000]](https://i.stack.imgur.com/4jWTC.png)
We see that the narrow wiggles caused by the fifth term in the series are producing derivatives that flail from $-40\,000$ to $40\,000$ everywhere, with tiny variations from the previous terms.
Let's get the same four pictures for six terms.
![W_6(x) on [-3/2,3/2]](https://i.stack.imgur.com/EjVqO.png)
![W_6(x) on [0,1/25,000]](https://i.stack.imgur.com/v4zf1.png)
![W_6'(x) on [-3/2,3/2]](https://i.stack.imgur.com/opkDX.png)
![W_6'(x) on [0,1/25,000]](https://i.stack.imgur.com/bikP1.png)
For the function, $W_6(x)$, the sixth term adjusted the function values by $\pm 0.02$ or less. For the derivative, the narrow ripples now have the derivative flailing from almost $-300\,000$ to almost $300\,000$ with very high frequency.
And the pattern continues as we take more terms -- $W_N$ approaches a continuous function and $W_N'$ tries harder and harder to make its graph go through every point on the plane.