ok, weird issue... while working on this:
i was in the simple Local Media view and arranged everything by length, so my short files of 00, 01, etc were first. double clicked the first one which it skips, let it play about 5 of the next ones, then double clicked the first one again, play ~5 more, then the first one again, and it crashes. happens every time. seems related to this bug:
not only does winamp not like and skip short files, if you try to play them successively, it will skip and eventually crash.
EDIT: i should add i'm using DrO's dll from the first link, but some of these short ones are flacs, and i doubt the DLL (meaning DrO's changes) has anything to do with it anyway.