Indeed, I've put assembled boards with more than a thousand holes in them. And I'm not exaggerating. And yes, I too use only Cleveland brand bits when working with HSS.You guys must drill a lot more holes in PCB material than I do, to wear out a HSS bit. I've drilled many hundred holes and still on the same bit. But then it's not a Harbor Freight bit either, but a Cleveland tool brand. While it seems like carbide is a good idea, for the DIYer they are a pain. In a PCB plant yes but home use, not worth the bother of breakage. Then there is the Cobalt steel bits that are harder than HSS but not brittle like carbide.
But even Cleveland bits will wear out after a few hundred holes have been processed. FR4 is a very abrasive material.