When you put in a narrow path of nice pavers, it enhances your house. If you put in a wider driveway of asphalt, it's an eyesore. Of course, if you take your unmown lawn with an odd hump in it and add lots of flowers in the sun, even an eyesore looks good.

Thank you for all the input, everyone! Looks like our best bet is to leave the structure of things alone and hope that paint makes some of the eyesores less sore. Landscaping will make a huge difference, too, and we're planning to spend a lot there. The front door is actually a mess when you look closely - hard to tell from the photo, but my husband and I who are 5'11 and 6'1 have to almost duck to get through it. It's much wider than it is tall, and I can't imagine where it would work. A fancy playhouse, maybe? 😜 We'll have to replace it anyway, so we're prepared to invest a chunk of budget there. As for reducing concrete, it's possible but would require regrading the hill to the side of the house. The concrete you see is a circular driveway, and it's the only place for guests to pull off the street. there's a narrow driveway that drives around to the garage, but it's really small already, and wouldn't be enough on its own. To eliminate the circular driveway, we'd have to widen the driveway that goes around back and create some space that way. Our house is in the country on some acreage, so theres room to do this, but the house is on a high point and the rest of the land drops off before leveling out again. I suspect that's why the driveway is the way it is now. May be a future project! I'm attaching a photo of the house with the faux windows circled.

I think we're all focusing on the sidewalk right now because it's the strongest visual element in the current landscape. Choose a design similar to Doug's that gives you something interesting to look at from inside your home. When planting beds and a couple of trees are added, you'll hardly notice the sidewalk. My real concern here is why the dog didn't face the camera when his portrait was snapped.

In general, I'm not a fan of replacing columns, but I think beefier white columns will look a lot better. Then, I'd paint the blue the same as the purple. After that, some chairs on the porch (blue to match the siding if you don't paint it and some pots of flowers.