I have tried about 5 different ways to format my files so that my embroidery machine can read it and it just won't. The file doesn't even show up on my machine. For reference, I am using a floppy disk to move the files and convert them into .pes as per my machine's specs. Am I missing a crucial step here or do I need to change equipment?

I am not sure which your exact steps were. But a common error when files don't show up on a machine (although the correct file format was used) is a wrong design size (too big). Some machines don't like if the stick (or in your case the disk) is filled up with too many files. So check on both of these points. The design size must fit into your available hoops.