This will take some time, and it's mostly dealing with old files, but some are from old programs I have. I have old versions of Windows that will run them. I know there are several ways to do this. What's best?
its unlikely you will be able to run any of the executables unless you run a virtual machine with a very old version of dos.
reason being 64 bit o.s doesnt support the old 16 bit installers.
data files on the other hand like pictures and music will just copy straight over as long as you can attach the hdd via an ide ribbon cable. as all windows current windows versions still support the older filesystems.(as far as i know)