Moving Installed Programs

[Hatefulsorrow]

Ok here's my delema.

I have a client computer that needs some programs moved to a new computer. His harddrive is going out and only has about 3 or so more starts left. He doesn't have any disks or backup. They cannot be replaced due to no longer being produced by his company. His is required to have these programs to stay in business. I need to know the best and most speedy way to move all of his installed programs from one drive to another and then to his new OS. Is there any program that can do this, a cross OS transfer of installed programs, and if not how would one go about doing this by hand. I understand that reg files would need to be moved as well as any program related files. I would like to avoid doing this by hand as it would take quite some time. Is there any programs that can tell me the location of these files and reg keys or do i have to search by hand. I would like to make such a program if there isn't one. So any suguestions would be cool too. Also any coding tips. I know a moderate amount of VC# so yeah. Ideas?