1. Go in to the Control Panel, select Administrative Tools, Event viewer, open the Hardware and Applications records, and it should give you an idea of where the problem lies, (Double click the error message to get more details) and where to look to fix it.
2. Is it just the program that hangs or the whole computer, if it is the program, then you may need more memory, as from what I gather Cakewalk is very memory hungry, if it is the computer then it is more likely a memory conflict, and will show up in the event viewer.
3. Right click My Computer, select Properties, Advanced tab, Performance settings, Advanced tab, Virtual Memory Change, and make sure it is set to either system managed size, or at least 3 times the amount of memory you have installed. If you have more then one drive or partition, then move the paging file to a drive or partition that does not contain the operating system.
Hope this helps.

Bill