I've been building PCs since XTs came out, and I cannot think of a single
time that I've reamed out a screw, with the exception of one of those very
fine pitch thread screws the CDROM manufacturers seem to like. If you're
re-threading the hole everytime, perhaps you should take it a little easier
on the poor PC case :-)
I've found it often helps to turn the screw 'backwards'
(counterclockwise) until you feel the threads click into place, then
tighten it.
In the case of self-tapping screws it generally pervents the screw from
starting a new thread (which, if done enough times means there's no metal
left). In the case of large-diameter fine pitch threads (like lens
retaining rings in cameras, OK, off-topic, but I can't think of such a
thread in a computer), it helps prevent cross-threading.
I assumed this trick was well-known, but perhaps not.
-tony