Hi Steve & Brad, A pretty good summary of how to format your MIDI files for playback is found in another thread (linked below), but here's the most important thing:
Right Hand defaults to Track 3 (assigned as Treble Clef)
Left Hand defaults to Track 4 (assigned as Bass Clef)
Strip any accompaniment/duplicate/multi-octave notes from those tracks to focus on the basic parts to play along with.
(Some songs may show up correctly in Chordana but plays a different track's part when transferred to the keyboard's memory if you don't use the default tracks.)
I've starting using Cakewalk again recently to edit MIDI files for my kids' LK-S450, and it can be a steep learning curve... especially trying to simplify complex songs. Good luck!