Note that most print title boxes include the phrase: "Do NOT Scale Drawing"... which means (to the user) that measurements taken from a print are not likely to be accurate. Perhaps even in relation to other measurements on the print. This can happen if printer skews media as it feeds. So. Dims are Very important in any application that uses hard-copy drawings (such as most contracts).
AutoCad dimension commands are straight-forward, so I will take your post to mean what to dimension and how. How is best approached (these days) with reference to ISO equivalent of ANSI Y14.5M, "Geometric Dimensioning and Tolerancing" unless your field is AEC (in that case, see Architectural and/or Civil standards. Properly applied dimensions define all characteristics of the subject with only ONE possible interpretation. Mistakes? Under-defining or over-defining the subject, dimension references that are 'theoretical' (do not physically exist) and inappropriate accuracy specification (such as 14.444 degrees). The drawings must be usable in the field or shop.