Hi scrappy, I agree you should do mockups for best visualization. In our area, the homes that are similar to yours- most paint their garage doors to match the siding color, and seems the most pleasing. Those that choose to paint their garage doors to match their front doors, most commonly a black or a dark color, end up with a garage that looks llike a big black hole. On my monitor your siding and trim look fine, but it may look alot different IRL. I like it as it, or if it seems mismatched to you, try the white trim idea, but I'd keep the garage door to match the siding and agree to paint the boxes under the windows all one color, no outlining. Also agree your front door/entry would stand out, and look more inviting if you painted it a pretty light/bright color.

What a beautiful home! I would make sure the finish relates to another finish on your home. Black picks up the shutters and fence, but it’s a lot of black. White would be gorgeous, as well. I don’t see any other wood, and given that it’s pine (am I correct?), I’d just paint it.

To me, the house doesn't look like it's stuck in any decade. I agree with Sarah to paint the garage door same as the house. Generally, why pick out the garage door of all things to make some kind of color statement? Save the colors for the entry door, and you didn't ask but I'll tell you what would do wonders here: Choose more substantial exterior lights on either side of the garage door, and near the front door, and add a big pot on either side of the garage door with colorful (or green) easy-growing plants in it. Then line the walkway on the left side with a planting bed, or a small hedge, to draw a visitor right to the front door.

“We want to work WITH the brick and not paint it.” You don’t know me, but I love you. Your brick is so cool and interesting, and you’ve done a great job landscaping. I love your little courtyard area — when I was a kid, those were popular and I miss them. Ok, a color. Can you show us a close-up pic of the brick? Do you prefer lighter colors or darker? Will the windows be painted, too? We are lucky to have very talented posters here who can do mock-ups of exterior colors … I hope they see this. I saw this and it reminded me of your brick (maybe):