My Dad was the RIO in F4s for most of his career in the Navy. He talked about flying supersonic with ord. He explained to me then about how they could not carry ords and fly in excess of a certain speed (what exactly I do not remember, only that it was subsonic). He told me anything over that speed and they would rip the ords right off the wings. From what I have seen here in Iraq, I would say that still holds true with the F15s / F16s. Although they approach at a much higher speed than, say, a P38 or P47, it is still subsonic. Perhaps this is different with the F22 as it carries its ord internal but the same logic applies in my mind, they would have to be subsonic to release.
I do not believe the yield from a 500 lber has changed much, only the accuracy. It is the accuracy of them which makes them so devastating. In the first Gulf War, the amount of ord dropped to kill one target was tons less then the same amount required to kill a same type target in WWII. I do not pretend to know the particulars of bomb making (way outside my lane) but I do know this. The military is using stuff from the Vietnam era in Iraq (I have had 7.62 linked with 1967 production dates). As the Military does not like to waste its ord, I would guess the same is true for the bombs. Just attach a "smart" guidance system on one and *poof* no more dumb bomb.
my 2cents
Tom