Small world.  I’m as far south as you can go on the mainland, and head to The Keys most every weekend.  Gilbert’s, to around Hog’s Heaven, or Islamorada Fish Company / Morada Bay area, usually.  Occasionally further, like when ‘Irma’ came to town.  I also have 3 H9’s on the ‘board, under MIDI control.

You can mine MIDI to great depths, or keep it simple.  What are you picturing?  Maybe preset control switching only, with all the MIDI-capable devices?  External loop switching, over the non-MIDI drive / distortion pedals?  Individual parameter control, continuously variable, under an expression pedal sweep?  Your answers will help to narrow down the recommendations

There are a ton of options out there now – simple to complex; relatively cheap to expensive.  I’d suggest a relatively simple approach to start, and a device with the capabilities to expand as your MIDI knowledge does.  And I know what you mean about the venue space, so compact is a priority.

Nice “second” ‘board.  But hey, your ‘baby girl’ is always going to be your baby girl.  I can’t really speak to your drive / distortion choices, from personal experience.  The Keeley has no pedal match.  I will say that a good analog or two makes perfect sense in this local market.  I drifted away from being a real purist, as digital distortion is getting so much better now (for my purposes).

But with 3 H9’s … you can cover most any sound or configuration that you can dream up.  Under MIDI control, the sky is the limit.  I run a small rack, big ‘board, stereo amps / FRFR, complex control, and I lug around an FCB-1010 alongside the pedalboard.  Not something I’d push on anyone else, but it works for me.