So the brick is already painted (yes, unfortunate), so I must paint. The windows/trim will be white. Should I keep the corbels and portico white to match soffit, and then do a medium gray body (any SW color options??) with either a black, charcoal, or bright blue or red door?

FYI Romabio is good at what they do ... no argument here.... but they have a limited range of only whites & very light grays and it cannot be applied to anything with conventional house paint on it, only raw unpainted masonry or other mineral paint applications. There are several other mineral paint (aka potassium silicate) paint co's in the US, a couple of which have a sort of "primer" product which can go over conventional paint - try this is one : https://www.beeckmineralpaints.com/ For best results though I think Id still want to get off as much of the paint film as possible .... but without going too far and damaging the brick. Then the primer product, and then the mineral paint. Of course this would be hugely labor intensive or expensive to hire out, that is assuming you can even find anyone who has heard of mineral paint or would want to do it. At the very least find a person who understands the science about this and doesnt shrug off the concerns - maybe there are some other types of breathable coatings that I dont know about. Michelle above is correct - any coatings need to be breathable, or there WILL be damage, its only a matter of time. The brick bldg across the street from me was painted only 12 yrs ago and is already spalling (ie brick cracking and disintegrating) terribly in some places near bldg exhaust vent and other places Its really sad how the big box, do it cheap mentality of the last 30-40 yrs has resulted in so much shoddy workmanship that is now considered the norm.... and actual physical damage. Not many people thinking long term any more, beyond 10 or 20 yrs.

I think you need two colors due to the half-timbering bit. But they can be very similar like the ones up there now are similar (or maybe they're even the same). The stucco in the front peak, shingles in the back peak, and maybe the eaves would work as a slightly lighter version of the main color. Not for contrast, but for depth. I like the slatey blue greens. Might even be able to go a bit towards purpley. Do get big sample boards. Huge ones. Bigger than the ones I used to pick my last house color. :)

Agree with removing the shutters, matching the brick color (or slightly darker) for the extension (and the garage door and the downspouts where against brick/siding), removing the tall shrubs near the house and trimming the rest, adding drifts of varied plants in deeper beds that create long, gently curving lines, within which the house rests as a sculptural object. Soft, creamy white that relates to the brick (not bright white) for all trim, including the broad horizontal band above the windows. (Can't tell from the photo whether that is actually the same color now or not.) I personally like what looks like a black door on this side and would do black on the garage side too. Love your Spanish moss!