First thing I would do because I really dislike asymmetrical front doors with a single sidelight: Replace the front door with only a door & no sidelight. If that door is less than 36" then absolutely a wider door. Center the door in the opening and then trim it out with wider/ beefier trim to hide any needed infill.

I would leave brick as is and replace the wood and horizontal siding to match. A sagey green would work nicely with the brick. Or pick an earthy, darker color from the brick for the siding.

Can't see enough detail on the chimneys. Either paint them or, if made of brick that matches the front brick, get them blasted/ restored to original.

Remove the shutters on the first floor and replace the louvered 2nd floor shutters with raised panel ones.

unify the color and you won't notice the contrast.

if you plan to make significant changes, I would start with the roof.

the lower roof, regardless of any color you choose will dictate the siding color, it is so prominent in the overall elevation. Are you using the chimmneys?

removing the brick would be major, I would work with it.

@ci_lantro and @Lyn Nielson Thank you for all the guidance so far. @Lyn Nielson yes, I will be using the chimneys. I had a thought that they could be covered in bricks (believe they are concrete blocks covered in stucco right now) But now that I think about it, that might be quite expensive, and maybe I should stick to other things. Any ideas for the big blank space over the garage door? @ci_lantro thanks for the color suggestions, when changing the door style would you also prefer changing the color (lots of brown)?

Here's a thought on Shingles

Certanteed Sunrise Cedar is an interestting mixture of good colors... lighter rather than dark,

as sun reflects rather than absorbs... we need to work against the Sun in summer and lighten the AC load, makes sense. Heat is a bigger problem than cooler temps. ...as far as your question on the garage roof, I wouldn't do anything since you have a chimmney on that end too.

But I would square up the corners on the door trim. if you are going to change out the front door, change out the garage door to compliment. at least you have good landscaping and hardscape in place.

You could do a pergola over the garage door