Will it be possible/feasable to load waves of “synth pads/chords” into the beatbuddy and trigger a chord progression?
Yes. You would need to make a custom drum set and load the wav files into it. Then you would need midi files which trigger those wav files to be loaded into a song.
What about having BeatBuddy to play several MIDI tracks simultaneously?
Not currently supported, but a possibility for a future update.