If you sign up for Yahoo! Briefcase, that you would have to upload everything that you want to keep, and then download them. This can be very time consuming depending on your internet speed, and will not work for programs. What you will need to do is to create a yahoo account. Then you can start using it. I think if you have a yahoo mail account it will work as well.
As a few of us said before, Windows based programs are dependent on more than what is in their Program Files folder. They have shared dependencies, and system dependencies located in different parts of the hard drive. Some of the programs have services that need to be running, or registry keys.
I work IT at a university (as well), we have users that ask us if they can do what you want to do. The answer is always No. They don't believe us, try to move it over, then complain that their computer does not work. They copied over the data from one computer and put in in the new computer. Tried to start the program, it said there it needed a file or there was an improper version. They search for the file on the old computer, and copy it to the new overwriting files usually in a system folder. And when they start the computer, they get a bsod.
I try to explain to them that it does not work, they think that they know more than me, and do it any way. It fails, they come back for us to fix it for them. The only way we can fix it is to do a repair install or a fresh install.
Yahoo! Briefcase will be good for your pictures, movies, music, documents, etc. But again, will not work for transferring installed programs.
The time it will take for you to upload the programs, and then download them again, will be more than installing it from the CD and typing in the serial key (if needed). The latter, is the best way to ensure proper functionality of the program.