I have never had a problem drilling and tapping the holes for the lock nails(screws) using the normal tap drill and tap. Of course, I don't normally use an 8-32 screw in the bolster. I use a 10-32 in the bolster, and an 8-32 in the front of the lock, through the web between the barrel and the ramrod hole.
I mark the hole locations with the lock in the gun; drill the holes with the lock out of the gun using a drill press and then tap the holes through the stock with the lock in the rifle. I may have on occasion, countersunk the holes one thread on the inside of the lock to facilitate installing the lock nail. However, I don't do it as a normal practice.
I can't speak to what problems others may have. The only problem I ever have installing lock nails is with the barrel being a little out of position such that the rear lock nail/screw doesn't want to go through the recoil lug. Usually, a rap on the muzzle with an assembly hammer takes care of that problem.
Now, if I didn't carefully "feel" the taps through the holes a thread at a time, with tap free, I would break them. It is just a difference between it taking a minute or two to thread a hole as opposed to less than a minute if I just tried to ram it through. I think I have only ever broken one tap threading a hole in the lock plate for a lock nail/screw. Normally, I break taps in a blind hole.
Of course, as Bill said, you do what works. Problem solving is part of making anything. So, if you find you need to go up one wire drill size, by all means do that. There is no orthodoxy about these things.