Robert wants to refresh his Windows PC without losing any programs that he doesn't have discs for anymore. Leo says he's going to lose them, and there's no way around it. There are some apps that claim to move software over, but they don't really work all that great. It's very hit or miss. He could install another version of Windows and have two OS installed, but that'll take up a ton of space. If he has a secondary drive, and installs on that, then that would probably be the best way short of tracking down the program itself.
Another option is to take the existing install and turning it into a Virtual Machine (known as Physical to Virtual). He can then install a new version of Windows and then run the old install virtually using Virtual Machine. That would likely be the best way to go. Robert should check out VMWare.