I think the real question is, given that we are going to put two holes in a tree, is it more profitable to drill the second hole after the first dries up, or to drill both at the start of the season.
Based on some (incomplete) information, if you are getting a quart of syrup per tap, then you might hopefully expect to get a cup of syrup from a successful ream or re-tap. IF the weather cooperates. So the yield on your labor is maybe one-fourth of that from the original tapping. Probably less.
Whereas, you might expect a pint or more from an "original" second tap. (Buckets; I have seen no data relevant to a vacuum operation.) And less labor than making a delayed second tap.
To expand my my original posting slightly, there are reasons to think that a second delayed tap, placed vertically above or below the original tap, located within the compartmented region resulting from the original tap, would
a. Produce sap, and
b. Do little additional damage to the tree.