Grass vs turf does make a difference here, I think.
Turf field... no crown of the field to speak of, nice, well-marked, straight lines... probably no need to measure in almost all situations.
Grass fields can have a lot of variety of playing surface... some of them will have a huge crown (I've worked on one that appeared to have nearly 3 feet of drop from the middle of the field to the sidelines). Some will have marks for every yard, some won't. Sometimes the lines won't be quite straight. In all likelyhood, my WH will signal for a measurement on a grass field if there's any possibility that it's within a foot or two of the line-to-gain.
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