First thing was to caulk the seams between the chimney and the shingles, from rooftop to ground,
Next, powerwashed the awning and blue-taped the edges of the door and utility meters.
Trimmed-out the edges before using paint-roller on larger areas.
Upper part is new paint, lower is old.
The finished product, as seen from the front corner of the property.
Finished, as seen while standing between the backyard deck and fence there.
I'm not going to bother with painting the back of the house. I've done three sides of it and that's enough. If the next owner of the house decides to add any extension on the house, it'll have to be added in the back, so there's not much sense in painting it. The back is the original, lighter shade of gray, but it is clean and really doesn't need repainting.
My work here is done.