FWIW my finish program went like this.
I had the holes drilled/filled/redrilled before applying truoil.
I put on one good coat of truoill sealer filler, about 3 or 4 of truoil and sanded with 400. It readily went back to bare wood in patches, so i rethought and put on several thick coats of sealer filler, sanding just the high spots between coats with 600 until i was confident it was thick enough that i could safely take it flat with 400 wet.
Only then with no visible shiny bits and no bare wood did i go for tru oil. Much the same with tru oil, 3 coats in short space of time, then sand back high spots only with 600. After about 4 repeats i wetsanded flat with 600, 400 for worse bits, then left for about two weeks.
Quick sand with 1000 and 1200, then burnish with abrasive car polish.
Compared to most folks I think more layers sealer thinner, rather fewer tru oil. Most important thing was a movable desk light so i could monitor reflections and easily spot as soon as an area had all wipe marks sanded off.
I trusted truoil /sealer to protect the end grain in the holes while wet sanding, and redrilled after burnishing. Also I used no more water than necessary. Dampened surface then frequently washing dust off the paper and wiping surface with a rag rather than flooding with water.
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