Where did you get the Crossover bottles? I have tried D2 with Crossover in Lion and had a hard time getting it to play properly.
Basically I made a XP bottle in crossover. Then loaded up the window's parts of each disc and installed that way direct into the crossover bottle.
Here is a link of more detailed instructions I wrote up on how to do this.
https://forums.macrumors.com/threads/1322754/
You need the -w command line to play D2 in windowed mode. I'm not sure if this is in the link I shared.