Finite trigonometric sums is a challenging and often quite difficult object of study. In this paper we investigate the finite sum of cosecants ∑csc(φ+aπl/n), where the summation index l runs through 1 to n−1 and φ 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 ∑csc(πl/n) does not have a closed–form, i.e. a compact summation formula (similar sums of sines, of cosines, of tangents, of cotangents and even of secants, if they exist, possess such expressions). In this 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 2×10−9 for n⩾10 and lesser than 7×10−14 for n⩾50, 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 summation formulæ for the digamma function). Asymptotical studies show that these sums may have qualitatively different behaviour depending on the choice of φ and a. In particular, as n increases some of them may become sporadically large and we identify the terms of the asymptotics responsible for such a behaviour. 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 formulæ, including some formulæ dating back to the XVIIIth century.