Files are easy, programs should be reinstalled. Depending on the licensing for the software you may need to purchase additional licenses.
I'd be leery of any software that moves programs. Back in the DOS days you just copied the directory where the program is installed. Once we got into windows files are placed all over the drive and entries made in the registry.
I look at a new machine or new OS load as an opportunity to start with a clean slate. By only installing the software that you actually use you cut down on some of the issues you have.
Your user files are stored in C:\Users\USERNAME, where USERNAME is the name of your user account.