In this paper we investigate the finite sum of cosecants $\sum\csc\big(\varphi+a\pi l/n\big),$ where the index $l$ runs through 1 to $n-1$ and $\varphi$ and $a$ are arbitrary parameters, as well as several closely related sums, such as similar sums of a series of secants, of tangents and of cotangents. These trigonometric sums appear in various problems in mathematics, physics, and a variety of related disciplines. Their particular cases were fragmentarily considered in previous works, and it was noted that even a simple particular case $\sum\csc\big(\pi l/n\big)$ does not have a closed-form, i.e.~a compact summation formula. In the paper, we derive several alternative representations for the above-mentioned sums, study their properties, relate them to many other finite and infinite sums, obtain their complete asymptotic expansions for large $n$ and provide accurate upper and lower bounds (e.g. the typical relative error for the upper bound is lesser than $2\times10^{-9}$ for $n\geqslant10$ and lesser than $7\times10^{-14}$ for $n\geqslant50$, which is much better than the bounds we could find in previous works). Our researches reveal that these sums are deeply related to several special numbers and functions, especially to the digamma function (furthermore, as a by-product, we obtain several interesting summations formulae for the digamma function). Asymptotical studies show that these sums may have qualitatively different behaviour depending on the choice of $\varphi$ and $a$; in particular, as $n$ increases some of them may become sporadically large. Finally, we also provide several historical remarks related to various sums considered in the paper. We show that some results in the field either were rediscovered several times or can easily be deduced from various known formulae, including some formulae dating back to the XIIXth century.
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