We bought our house a few years ago and focused all of our attention on the interior. We're finally preparing to do something about the exterior of our house. We met with a painter this morning to look at some paint that is peeling on the back of the house and the condition of the paint throughout the house is in worse condition than we thought (these photos are a few years old, but the only thing that's really changed is that the paint has gotten worse). Before we bought the house, the previous painters have appear to have done a pretty shoddy job (not properly priming and caulking the wood siding). So now we're looking at repainting the entire exterior in the next six months or so. This isn't the end of the world, since I don't like this green color, but this means we actually have to decide what to do.

Option 1 would be to just go ahead and repair the damaged siding immediately (just in a small section of the house) and repaint the entire house early next year in a better, to-be-determined color, but abandon plans to make the exterior look less boring. We'd probably also replace the front door.

Option 2 would be to repair the damaged boards asap, but undertake a more extensive exterior remodel to replace the siding with something that looks better / more interesting / more modern. Given that we're working with a tall, skinny box, I'm not sure that there's too much we could do here to make things look substantially better without a major amount of structural work (which we're not interested in). I haven't had much luck finding inspirational photos updating a house like this. But, perhaps there's something I'm missing.

Does anyone have any suggestions / ideas for how to give a house like this a more interesting facelift?

Thanks!

The back of the house is accessed via an alley. The boards under the sun porch are the ones that need to be replaced due to damage.