Aesthetic considerations aside, can you imagine how you would plant, maintain and water window boxes at that height? You'd need to install automatic watering and climb a ladder or hang out of the windows above for the regular maintenance they would need.

Decent looking house. I think the garage doors and trim are your only issues. Either the color of the siding to blend in or dark like the trim, but dont create the box effect with the contrast.

Eta - frost the garage windows with the kit from HD.

What is it you want to change about the trim?

some ideas:

https://www.houzz.com/discussions/advice-on-changing-paint-trim-and-doors-to-brighten-up-house-in-pnw-dsvw-vd~5364772?n=11

It's best to have only one dilemma for the same subject.

The tall shrubbery near the walk and in front of the door view are anti-welcoming. It'd be better to get rid of it and keep lower plants in that zone. The front yard seems to be separated from the street with tall shrubs, which also happen to surround a bald spot in the yard. It seems like you need groundcover, and less separation. If you cut some things down so the house can be seen, come back with new photos so we can see what might work with the house.

The number one issue is the overgrown shrub on the right. Trim it way, way back. Then post a picture so we can actually see the house.

The other thing that jumps out at me is the jumble of stuff at the right-hand side of the driveway. I can't really tell what's there - a hose caddy, a small pot, some pieces of lumber, a few rocks? Clear all of it away and then place ONE BIG pot there with a green plant/plants in it. It doesn't have to be a round pot; you could do a square or rectangle one if you think it would fit better.

I have seen a few split levels in our neighborhood updated with a gable roof and posts extended to the edge of the concrete entry. I'll see about getting a picture posted of one maybe.