KarinL, you've given me tons to think about. Here are some thoughts in response to parts of it: Your questions about how I want to move through and be in the space are well taken. I'd add another consideration, though, which is how the house speaks to the street. I'd like it to say: "this bit is my yard, but please do come in! Because of the walk, the porch steps, and the deep front porch, the way in for visitors - and the way I'll walk in and where I'll put down groceries - are very well defined. Here are a couple of pics that show more of the front yard: Because of the way the holly tree (which I love) sits on the west side of the front yard, there's a real imbalance between very strong and rectilinear visuals on the west side and open and scraggly boundaries on the east, the more so with with fence coming down on the east side. I'm cool with the openness on the east and the more closed, divided feeling on the west, because I love my east-side neighbors and not so much the west-side one! That said, I do feel like there's a need for some visual interest and definition at the property line on the east side - something just a little sheltering to reach out from the side of the house towards the sidewalk and embrace visitors without overwhelming them. Which leads to your next point about... Planting along boundaries: The caveat against the beginner's mistake makes sense to me, because of course in interiors the comparable mistake is to line up everything absolutely straight against the walls. In this case, though, having lived in the house only a short time, I can clearly see the need for some definition along the property line but don't yet fully know how I'll want to move in the space. Since whatever goes along the side and back of the yard will be visible over whatever eventually goes in the middle, is there any harm in planting shrubs near the outside edges of the space and making decisions about the middle in a future season? On the hedgy stuff in front of the porch, I do have some useful info, and I think you're right that most of it has to go. There are several different things going on there. The low thing out in front that's trimmed like a hedge is a group of azaleas! Now, I like azaleas, but these flower in the worst possible shade of magenta for all the other color that's going on here. The largest thing is a red-tip photinia and most unfortunately it's falling victim to that leaf spot disease. Poking up between the azaleas and the photinia are a couple of very happy rhododendrons, which could stay and become part of a new grouping. I'd love to look out over something pretty when I sit on the front porch, but I don't need something that screens the porch as much as the current ailing photinia does.

I don't find that house to be ugly. It says small town craftsman's special to me. It's certainly not cookie cutter design, which IMO is ugly. My father grew up in the house his grandfather had built: small, poor layout, but still going strong over a hundred years later. There is more character in that kind of house than in any McMansion with superficial bling. Just be aware that the price is low for a reason. Money will need to be spent on other things before you can pretty it up on the inside or out. Looks like it needs a new roof and definitely gutters, so there's a chunk of change right there. Can you afford a paint job after getting the house waterproofed? Here it is in gray, a blue door, & the awkward shrub cut back:

Yes those V shaped things at the top of your post should be removed. It shouldn't be difficult. Your hanging baskets need to hang lower. Go to your big box store and have them cut you some heavy chain in about 1 to 1 1/2 ft length to lower the baskets. Most baskets need to be watered at least every 2 days, some times every day depending on the weather. Also once a week submerge the whole basket in a bucket of water and let it sit for a half an hour to an hour to re-dehydrate the soil. I like the idea of a yellow front door and yellow flowers. It is only paint. Tell the hubby if he doesn't like it, it can be repainted. Take him with you when you go pick out the paint and have him pick out 3 yellows he likes and then you choose between them. That way he has a stake in the color. If you don't like any that he picked out just buy the color you like and wait a few week to paint. Then when he says it doesn't look the same just tell him it is hard to visualize a color from a little paint chip. Lucky me my husband lets all the decorating up to me. If it was up to him he would buy a 5 gallon bucket of white paint and paint everything in and out the same.

wondering if someone WANTED a crafstman style and did the brick work, and never added the roofline? It looks like an overhaul if you want to continue the porch style to include the pillars. It would also require removing the portico overhang that already exists. How much of an investment are you thinking??? If it were mine, and I was replacing shingles, soon, I would replace the roof with a taller pitch. at that time, I'd add the required porch roof to accomodate the existing pillars and create a so called craftsman style. Is it worth the effort and expense??? Is the brickwork stable enough to re use? Something to think about. with all that said, I'd remove the Bricks and build a nice composite deck, create a cute cottage look. You asked.