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tape measures are generally just a bit less accurate than getting verniers on stuff
Yes, I'd measure from bead seat to desired spoke end (by inserting a nipple into a hole) with the best depth gauge to hand. For most people that is going to mean the depth stick on a digital caliper, but a vernier or a depth micrometer will do just as well. You do have to be careful with tubeless as the bead retaining lip will influence the measurement, but you're only aiming to nail the spoke length, so nearest whole mm is close enough.
Nah, on clincher rims measuring from the bead seat (which is nominal size ±0.5mm or better) is easier and more reliable, since it is not affected by any non-circularity of the loose rim