Although I love "painted lady" houses, the choice of colors with the brick from the previous paint job were wrong for the brick. IF you should decide to not paint the brick, a calm grayish blue would work nicely I think. I also think that gray would be too drab and dull unless it was a gray that suggests blue or green, with white trim -- but not bright white. I love plum as a rule but not sure about it here -- maybe a more eggplant or damson shade instead of a bright plum.

Any way to get matching doors on the front?

Thank you @cat_ky, we're definitely planning to put in green plants after it gets repainted -- possibly a wisteria if it can work with the north-facing light!

Damson sounds like a great idea. We are definitely looking to get the doors to match in color.

Darker plum gray on outside and lighter neutral gray on the inside. You don't want the porch to be like a dark cave.

Thank you Emmarene for the photoshopping! I am actually considering Perle Noir by Sherwin Williams for the outside, and then origami white for the inside and the top of the house as well. Trying to find a third midtone gray that will work with those!

check out this blog about how the home owners painted their brick house and some of the new paint colors available from the paint manufacturer they used (specifically made for painting brick):

https://www.younghouselove.com/romabio-brick-paint-color-collection/

Right now the upper and lower parts of the house seem completely disconnected, and the door looks like an afterthought. I would keep the beautiful brick and paint the upper part a charcoal color from the brick, with cream trim for the details. Paint the door cream or a glossy black. I would suggest you at least try different colors on a visualizer to see the overall effect before you decide to paint the brick. Your home can be stunning!

Also consider staining your brick rather than painting -- helps with the long-term upkeep while getting the color change you want.

Are you able to remove or trim that large tree out front? You have a unique house but it's hard to see all of it to get the full effect.

As a few others have indicated, you may be able to get the look you want without painting the brick. Here's a few options that look nice with brick.

I know you are planning to paint the doors the same color, but I think raee above was asking about making the actual doors match. I think the one of the right is more in keeping with the age and style of the house. Obviously it won't have the transom but the same kind of door with the 3/4 window would give it some cohesiveness.

Another option if you feel it is all just too much brick is to paint just the front facade or the porch interior but not both. I like the black interior as it really makes the doors stand out, but the lighter gray could work if you choose black or dark trim.