I have not seen much demo of midi guitar 2 with chords but it would sure simply things if it did well. I play piano and organ chords frequently. BTW I used GR33 for years, got a defective GR55 that did not track as well.
With gig performer, I am able to go from song part to song part, song to song instantly with the “next” midi button on my livid guitar wing. I play way more sounds than guitarists with a big assortment of pedals and yet- I have no pedals!
You should totally check out Midi Guitar 2. I’ve used them all. Triple Play, GR33,55,20, 30 etc.
It’s a game changer without hardware.
Check this out.
Although only using rackspaces and variations, I do exactly as you do but with a guitar + Jam Origin Midi Guitar instead of a keyboard and my pedalboard is just expression pedals and switches for MIDI control. 
It does chords too. I think there’s gotta be a demo online to check it out. Highly recommended