By looking through an book, I found this interesting series
To prove that:
$$\tan(\theta)+\tan \left(\theta+ \frac{\pi}{n} \right) + \tan\left(\theta + \frac{2\pi}{n}\right) + \dots + \tan \left (\theta + \frac{(n-1)\pi}{n} \right) = -n\cot \left(\frac{n\pi}{2} + n\theta \right)$$
I have tried the Gaussian pairing trick and using:
$$\tan A + \tan B = \tan(A+B) (1-\tan A \tan B)$$
And
$$\tan A \tan B = \frac{\cos(A-B) - \cos(A+B)}{\cos(A-B)+\cos(A+B)}$$
However I could not do anything of great use.
I also considered perhaps roots of unity of:
$$z^{2n} = \cos \theta + i\sin \theta$$
But that grew to no real use, but it may be an idea for others.
I know I can sum an arithmetic series of the arguments for the cosine and sine functions but I cannot find a source on the internet about the tangent function.
Thank You.