Problem resolved. :)
Got this thing taken care of myself.
Turns out that OOTP was, for whatever reason, looking in My Documents\Out of the Park Development\OOTP Baseball 9 for those files rather than in the program location. I specifically told the program that my data was in the program directory, but when I copied my stuff into the My Documents location it all worked.
So it's a bit weird, but I'm not going to look a gift horse in the mouth.