I almost got caught out with the leders kit also.
The trick with it is to start the softening process with lube before the skin dries off to much , every day (works for me anyway)
I use a 4x2 and just work the lube in with the end of the length of wood and just scrubbing around randomly on the ground with a fair bit of weight pressing down.
Your idea to redampen and relube might work if you try the 4x2 maybe.....
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