Nice job Doug!!! The one thing I would change is to lower the pink flowers that are hiding the front steps leading to the door and place matching shrubs on each side of the steps to frame them and make them more of a focal point. Making the steps a different color from the rest of the lower brick wall also visually "beef" them up. Right now they blend in with the brick color so your hardly see them.

The pink flowers are a red laceleaf Japanese maple.

I would leave the brick for texture and color but paint the siding a medium gray. DD's landscaping is a way to add some curves to all those angles.

So, you've got your plan! Full steam ahead!!!

I use Realtime Architect

Nice house.

Please don't paint the brick. Anything painted will, inevitably, need to be repainted and begin to look awful as it gets to that point whereas the whole point of brick is its low maintenance.

Removing the shutters permanently is a good idea. When you replace the windows, you could have an additional trim board added all around the new windows in lieu of replacing the shutters.

Vertical board siding to replace the current siding is also a good idea. If you're going with cedar, keep the natural wood cedar finish look rather than painting it.

If you use something like Hardie Board siding and paint it, paint your front door a bolder version of the same color.

Before growing season, you might consider cutting back the shrubs by the house, digging up the root ball and transplanting them to along the edge of your lot to make way for a front yard patio beneath the shade of the tree in your front yard..

You might outline sidewalk -- not necessarily with pavers. You could use a plant such as lirope -- something suitable for your geographical area -- as an outline.

https://www.gardenerdirect.com/buy-plants-online/3697/Liriope-Lily-Turf/Liriope-muscari-Royal-Purple-Royal-Purple-Liriope

Do sow some shade friendly grass and keep it watered and fertilized -- the lawn is a huge part of curb appeal.

Have you considered adding a deck or even a brick or stone faced patio in front of that left section of the house and around wrapping it around that left corner?