Installation for Dawn of War and the expansion Winter Assault required swapping out CD's. Testing with the 'Anthology' collection, I couldn't get Crossover to 'eject' the CD to continue installation
Workaround: Copy contents of each CD into one folder. autoplay.ini is on each CD so I kept CD1's and skipped the files from the rest of the CD's.
Now all that remains is to install software through Crossover using the 'select installation folder' method. Use this procedure with Winter Assault too.
However! Out of the box DoW v.1 ships with copy protection. This means that the game needs to have CD1 inserted to play. I found that Crossover wouldn't 'mount' the disk, meaning that DoW would return an official error and not load up.
The solution to this is to download the combo update from the relic site
http://88.198.39.149/~dowpatch/, all the way up to 1.51 installing as normal through Crossover. The good news is that 1.51 patch removes the copy protection meaning the game loads up without any further problems. (There are further problems with the CD key validation for online paly, but this error is covered on the relic site http://forums.relicnews.com/showthread.php?t=51566
Long winded, took me an age to figure out but the only waiting time for you should waiting for the patches to download.
Once in the game runs very very well on the highest settings. There can be a slight texture problem occasionally, but so far this has been intermittent and solved by reducing the shadow and light quality to 'medium' in the settings.
Tested on Crossover 7.0 in a win2000 bottle.
OSX 10.4.11