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.

This style of house was built by the thousands in Florida in the 60s and 70’s, often referred to as Bermuda Style. Usually painted a pastel color, always had shutters, and the quoining on the walls would have been white. Your columns look a little bit undersized to me, and a slightly wider staircase might be nice, but I think once you’ve landscaped you won’t really notice. They are so pretty when painted a cheerful color, and look wonderful with a colorful garden much like it seems you want. If you are far enough south, Hibiscus is a fantastic choice. It blooms all year, comes as a bush which you can even grow as a hedge, or as a Standard, for a more formal look. There are an almost unlimited variety of flower shapes, sizes and colors. Whatever you do, don’t get talked into Oleander, beautiful but toxic. Your house is going to look wonderful when you paint and get the landscaping in.

If the bottom pic is what the house looks like now, you've done a great job. In the spring, I'd plant annuals. They'll bloom all year and perk up your garden. Pick a color scheme. I might be tempted by white, pale pinks and dark purple to match your door. Plant lots between your shrubs. Get some matching cushions for your bench.