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Does it make sense to boot the connector onto the expandable braid sheeting if it will not be watertight anyways because of sheeting itself being porous?
I never have, though I have considered it a few times just for aesthetic reasons.
If it will make the particular harness look better in that install, go for it, if not, I wouldn't worry about it.
That being said, a boot can also provide some strain relief, so that would be another reason to consider it for some connections.