Sorry I'm late to respond here guys, I somehow lost track of this topic. Thanks for all of the helpful suggestions though!
Thanks, but I had read up a bit on PGP before and heard that Gpg4Win was not very secure. I guess you could say that about all Windows products though right, so anybody know if there's any basis to that claim?
That's one of the reasons I stated I know I might need to use a Virtual Machine or something.