You have a lovely home! The plans you have to remove awnings, remove current landscaping and change the mailbox and light fixture are right on target.

The one other item that pops out immediately is the gutters and downspouts. The downspouts jump right out because they are white. Can you paint them to blend in or move them from the front so they aren't quite so visible?

How modern do you want to go with the style of your home?
Or how eclectic?
Shutters have a tendency to be traditional rather than modern. If you like shutters, then I would suggest the top windows only - the bottom windows are modern and not designed for shutters at all.

Once you have done the above, then repost photos. You might actually find that you are nearly finished without having to repaint anything. :)

I would be more inclined to concentrate (after your initial changes mentioned above) on the new landscaping and the front door area rather than repainting your exterior for the most bang for your buck.

Consider painting the band that devides the upper and lower floors a dark color. Agree with painting the downspouts.

I would not consider painting the brick, if for no other reason than maintenance. I love ppf. idea of painting the band and Denita idea of painting the downspouts. I would remove awnings, spray paint mailbox same color as you paint the band and consider getting a full glass storm door so that the paint color of the front door can be seen. Maybe you can even paint the front door the same color as the band and the mailbox. Cutting down those tall bushes will also make the space fill more open and modern.

Can't see the 'true' colors of the siding and brick. The vinyl seems to have some pink tones in it.

Painting brick is usually not recommended- but if you do paint the brick, painting it the same color as the siding may make it blend too much.