I'll try to address this one anyway. The answer will be yes and no. It will be on a program by program basis. Typically, you will still have some files that will install under Windows and will contain entries in the Windows registry which are needed for them to function properly. So, if your intention for installing software on a portable drive is so you can carry the software to another PC as well, this is not going to work. You can use it to carry data from PC to PC but not installed programs. The factory built external you want depends on how it will connect. USB2 and Firewire are common. SATA is also possible. I can't recommend by brand as mine are just HDs in enclosures I buy. The major HD manufacturers make externals and any of these should be fine. If you have a brand preference for your internals, going with the same for the externals makes sense. Hope that helps.