While installing windows, remove the faux shutters and see how the brick looks behind them. They probably don't need to go back on the house. The window installers would probably be happy if you went ahead and pulled out the overgrown shrubs that will hinder their job. Change the front door style and install lantern lights that are 1/3 of its height. A wide walk directly out to the street will be more welcoming and landscaping can flank it.

Thanks @decoenthusiaste. Any thoughts on roof/trim colors?

Lots of yellow in the brick on my monitor. If that pic looks true to you, take it to the roofing showroom and drag some samples over to the natural light to check them together. I'm thinking it will have to be a brownish color and maybe creamy white trim.

I think that your current colors ( roof/ trim ) work well with your brick. Once the windows and roof are replaced I would replace the door and make that a nice color, perhaps olive green or a dark red?

I would look at gray roofs as well as weathered wood, nothing with a red undertone. I would do an off white trim. Also paint the door the same color as the trim.

Removing the overgrown bushes will have a big impact.

IMO a color close to the new windows as for the rest those shutters have go and all that overgrowth too. Then what is your style idea this house can go in a few directions so some idea of what you want will help.