I would propose an alternative way of removing the confusion here, which I learned from a mathematical physicist: Arguments to transcendental functions never ever have units. You must first convert the dimensionful quantity to a pure number, and only then can you evaluate functions on it. From this perspective, there is no "$x$ is in radians" or "$x$ is in degrees". The conventional $\sin$ function takes as input numbers (say, $\pi$) and returns numbers as output (say $\sin(\pi) = 0$).
If you want to interpret the "angle" $x$ as being measured by a different unit, then you are dealing with an entirely different function. Then there is no confusion. Let's call it $s_d(x)$ (d for degrees). So $s_d(0) = s_d(180) = 0$, $s_d(90) = 1$, etc. It is easy to see that for all $x$, $\sin(x) = s_d\left(\frac{180x}{\pi}\right)$. But now there is no way to be confused:
$$\int_{0}^{180} s_d(x)\,\mathrm{d}x = \frac{180}{\pi} \int_0^\pi \sin(y)\,\mathrm{d}y$$
$$\int_{0}^{\pi} \sin(x)\,\mathrm{d}x = 2$$
$$s_d'(x) = \frac{\pi}{180}c_d(x) \quad \text{(where $c_d$ is "cosine measured in degrees")}$$
There is no contradiction between the second identity and the familiar $\sin'(x) = \cos(x)$. $\sin$ and $s_d$ are different functions and you should not expect them to have the same derivative.
In the comments you ask:
Say if my velocity was given by $f(t) = \sin(t)$, with $t$ in degrees, would my displacement from $t=0$ and $t=180$ be $\frac{360}{\pi}$ or $2$?
I claim this is not a physically meaningful question. You say $t$ is measured in degrees, but you also say that your velocity is one-dimensional. Those two statements are inconsistent, because in one dimension there are no angles to speak of.
However, there is a physically meaningful situation that is close to what you said. Imagine a particle moving at a uniform speed around a circle, starting at the bottom and ending at the top. If the particle has unit speed, then the vertical component of the particle's velocity will be $\sin(t)$ whenever the angle of the particle from the (downward) vertical is $t$ radians. If the angle is in fact $D$ degrees, the vertical velocity will be $s_d(D)$. At every instant of the motion, if you have equal angles $D$ degrees and $t$ radians, both formulae will give the same answer.
Similarly, the vertical displacement of the particle at each instant will be $\cos(t)$ or $c_d(D)$, again depending on what system of units you choose. The final displacement is $2$ no matter what system you choose (as should be physically obvious).
But isn't there a contradiction there? Why do I differentiate to get the velocity when I measure in radians, but not when I measure in degrees? Why doesn't integrating the vertical velocity give me the displacement when I measure in degrees?
The answer is that you are not using the displacement formula correctly. The formula $v(t) = x'(t)$ presumes that the independent variable measures time in the system. But if your velocity is measured as a function of degrees, then you are not using absolute time as a parameter - you are using a scaled version of time, and the formula for calculating displacement from velocity is different in that case.
If you do choose time as your parameter, then you happen to get the same formula as if you measure in radians. This is one of the reasons physicists choose to use radians in their calculations.
(An interested reader may like to read the wikipedia article on Dimensional Analysis).