This is an awkward question. Some people are lucky and play SS2008 without problems with Windows 7, others have some problems.
I can play many of the missions without any problems on my machine, but some missions fail to start and the message:-"Questviewer has stopped working" comes up and then it crashes.
See the following message from Mad Fred the Administrator:-
http://forum.shipsim.com/index.php/topic,16704.msg219970.html#msg219970
This makes it clear that "let the buyer beware", SS2008 was not made to be compatible with Windows 7 in other words.
Regards,
Traddles.