Ditto to the christophern post. That primer will provide nothing but pigmentation at this point. It must be re-primed and using oil will negate the need for removing the chalking that is probably happening too. If you remove that a latex primer is OK as oil primers can be tough to buy in gallons in some places.

K Laurence - I agree, landscaping will make a big difference. I guess right now I’m hoping to make it as good as possible without doing any kind of landscaping, so it looks even better when I do. Not sure if that makes sense, but at least it will be easy to paint without trampling any plants. Gargamel - I thought about removing the shutters, as I’m not a big fan of purely decorative shutters either, but it almost looks unfinished. Below is a pic so you can see what I mean. Pennydesign - I’m interested in stain, but I feel like it might be strange if I just replace the flat pieces of wood with new flat pieces of wood, not sure if it needs an interesting grain or if that is worse- maybe I’m not thinking of the right material. Powermuffin - Got it, if I go with a grey exterior, would you go darker grey or black with the shutters - or something that would coordinate with the front door depending on that color? Emmarene - Good call on needing contrast with the roof and nice photoshop work! The left side of the house is definitely odd. After I paint the next step is landscaping (i.e. a big shrub). I am toying with the idea of removing the gable as well, but that wouldn’t be for a while as I’d be waiting until I got a new roof. I thought about making the cedar shakes level all the way across (pic below), but that looks odd to me as well - what do you think?

Thank you, everyone, for your comments! I guess we should remove the porch railing! Most of the aluminum storm windows are missing panes so I was planning to replace them with white vinyl when we paint. The windows are an uncommon size, though, so I'm a little worried about the cost. There are only a few original windows, but the "new" ones are from the 70s, so they're all old. All the windows are wood and painted white-- and they're ALL drafty and in need of re-glazing, which is why we need the storm windows! I'm adding a better photo of the front porch-- and the chickens. The color I picked for the front door is close to the color of the sky. sheepla-- is there also no hand rail on the steps of your porch? I'd love to see a photo!

The stone gives your home a casual country feel, so the rigid and formal hedges look very out of place. I would pull those out and install a more open and airy landscape using lots of native perennials that will thrive in your locale but not become invasive. The concrete planters are also of a different era than your country home, so remove them. Consider installing some landscape lights that highlight the stone. And since the stone is so massive, I would remove the little arch details on your porch posts and beef up the posts themselves so they have adequate visual heft to stand beside the massive stone wall and look like they can support your porch. Are you replacing the roof or cleaning it? I would take care of that before choosing a siding color, and I vote to remove the shutters. You should probably upgrade the porch lighting too.