Well Kevin, it will last longer, but, not forever. I have a piece of wood that I lay under anything I'm drilling, I move it around so that there's no chance of the wood getting a small blow-out from the drill passing through. I don't know if your idea will work or not, I suppose it could if you never move the press table, and as you suggested you always use the same sized drill bit. I use a backer when drilling, but, I still sand the back side of the cutting with an orbital sander before I begin cutting. I find that doing so, makes the piece of wood move more freely on the saw bed.
Len