Little by little, we are gradually making our way around the house, painting it (by the time we make it all the way around, it will be time to begin again, I'm sure!)
The issue with painting a house that is 140 years old, is the wood is so dry that it doesn't hold paint well, or for long. It takes a tremendous amount of prep work to get the surface ready for a layer of paint. We've had lots of people "offer" to come paint the house (like, spray it). I tell them, "the painting is the easy part - it is all of the detail work to get the surface ready to paint that takes time."
Steven is a perfectionist, so that means besides a thorough scraping off of old paint, there is wood filler used for any holes, bad boards replaced, nails fixed, cracks filled, window sills repaired or replaced, etc. Then hand-brush on a heavy sealer/primer, in order to really work it into the wood, caulk any seams and apply top coats. It takes days to get one small area done in that fashion. But we are trying to help the house last another 100 years as well as it did its first 100.
The photo below is of a small area we applied primer to this week -- such a difference! It will still need a couple layers of top coat, and then we put up the new storm window. You can't tell after the paint, but the bottom three siding boards are new - concrete board siding, to prevent the issue of the bottom-most siding always rotting out.
(On the left side, we haven't yet finished prepping that area - although we have finished the window).