I've tried playing both the new re-release of transport giant (2012 Gold Edition) and the original multi-disk retail release V1.0, under cross over recently. This is what I found. Installing using WinXP bottle.
Transport Giant V1.0
What Works -
Nothing won't install
What Doesn't work -
The installation program. Gets stuck at the insert disk two moment.
What I haven't tested -
Everything after the install program.
Transport Giant 2012 Gold Edition
What Works -
Installer
Main Game
Campaign Mode
Endless Maps
Virtually everything
What doesn't work -
Saving (This can be easily fixed to work - see below)
Changing the Resolution (This requires editing game files - see below)
What I haven't tested
Signals
Fixing the save issue
This is an issue on the game under windows as well. To fix it:
Open CrossOver
Go to configure > Manage Bottles
Click on the bottle you have transport giant installed to
Go to the advanced tab
Click on open C drive in finder.
Go to Program Files > Transport Giant Gold
Now create a new folder called "save"
Problem Fixed.
Changing the Resolution
Due to the graphics engine used the game will look bad if not played at the native resolution of your display. The problem is that the only resolution options available are very limited. Unless you have a 1024x768, 1280x1024 or 1280x800 display your going to be rather stuck.
However with a few edits to the games files you can have any resolution you want.
Open CrossOver
Go to configure > Manage Bottles
Click on the bottle you have transport giant installed to
Go to the advanced tab
Click on open C drive in finder.
Go to Program Files > Transport Giant Gold
Open file "tg.ini" in a text editor and add
0:Mode20=1680x1050x32x60:1 (Replace 1680x1050 with the resolution you want)
to the top of the page then save.
Open the "config" folder
Open the "GameStatus.xml" file in a text editor and change the display settings values to the following:
<DisplaySettings ScreenHeight="1050"/>
<DisplaySettings ScreenWidth="1680"/>
<DisplaySettings ColorDepth="32"/>
<DisplaySettings VSync="1"/>
<DisplaySettings Refreshrate="60"/> Again use the resolution you want in place of 1680x1050.
Now save the file and your all done.