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For handgun cases, I personally don't worry about case length and never measure unless there is some problem in chambering.
For rifle cases, unless you are into really competitive bench rest or similar shooting, the only thing you need to worry about is the case being too long. Your reloading book will have a "maximum case length" and a "trim to" case length. If a case exceeds the maximum, trim it back to the trim to length.
Once it is at the trim to length, it will take several (or many) firings to grow back to where you need to trim it again.
As far as measuring, the fastest way is to lock you calipers to the maximum allowable length per your manual, and then see if all your cases will fit through the caliper jaws. Those that will not need to be trimmed.
I usually work with batches of 50 or so cases at a time. If I find one or more in the batch that need trimming, I go ahead and trim the whole batch back to the "trim to" length. Make a note on the bag or box in which you keep your cases so you will know when you trimmed them, or use your own method to segregate trim date/number of firings so you don't need to measure the cases every time you reload them.
I check my 22-250 cases after every three or four firings; my 45-70 cases after six or eight.
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