Johnathan,
You already have that feature on the Tyros MFD--it's called favorites. And, you can customize the Favorites list and MFD using Michael Bedesem's Music Finder View program, or just build the list on the keyboard.
First of all... it should be easy to do in the keyboard instead of being done in a separate software solution. Does it put it in the order you want or is it alphabetical? Do you have to rename the songs with numbers i.e. 01-02-03??
Yes it can be done right at the keyboard, it alphabetizes them, if you don't want them alphabetized then you would have to rename them. You can add files to the mfd from the USB ports or the HD. I also create separate mfd files for different gigs. They are backed up, then easily loaded from the keyboard. Nice thing about separate MFD files is they have to be only as large as the number of tunes you may be playing at a particular gig. The result is let's say an MFD file with 75 possible styles, mp3/wav or midi files.