Another problem I am having is this. When I first tried to import, I went only with the .dat files to make it quick. However, OOTP would crash upon generating player pictures, for some reason. So, I imported with the player pictures intact. It works fine - I can change ethnicity, I can generate a new picture, it's all swell. But, the game crashes when I try to generate the same picture, or if I want to change a guy's beard. This is most inconvenient, as players will change teams pretty often, I assume. Forcing an update also crashed.
I'm hesitant to post an unsecured league file since it's an online league and I'd rather my owners not get access to the commish side of things, but if testers want to take a look at my files, I'll see what I can do. if you want to test it out outside commish mode, though, the OOTP8 (mac) file is available
here, although it's apparently clean under OOTP9 for PC.