I would suggest this approach:
1. Grab one of these:
http://www.newegg.com/Product/Product.aspx?Item=N82E16817153133
2. Boot ya new Windows 8 machine and partition it using EaseUS or some other free utility.
http://www.partition-tool.com/landing/home-download.htm
3. Pick say 128 GB for ya C drive ..... say 512 GB for ya Games Drive (D:\) .... 128 for programs (E:\).... whatever is left for data (F:\) ....or any other names / sizes that make sense to you.
4. Plug the BlacX into an USB port on ya machine.....put ya old HD in the BlacX and wait for it to be recognized.
5. Go into C:\ProgramFiles\ and copy the "MyFavProgram" folder from ya old drive to E:\ (Programs Drive) .... rinse and repeat with "My2ndFavProgram" and so on.
6. Your E:\Programs drive will now look like:
E:\ (Programs)
-MyFavProgram
-My2ndFavProgram
-My3rdFavProgram
-etc
7. Copy ya games over in a similar matter to D:\ and ya data over to F:\..... Again, names and how many partitions are what makes most sense to you.
8. You data will be fine .... a decent amount of your games will just run as is.....if not just reinstall them over themselves at their new location to set up registry entries. Finally, some programs are self contained and will run fine, but you will probably want to reinstall over themselves into same folders anyway. This will set up registry entries as well as create shortcuts and desktop icons if ya want. All previous customizations, saved games etc should remain as installer normally does not write older files over newer modified ones.