Hey all - I've got a finished side of my basement that has no windows. On one side, I could put a window that's about 18 inches high toward the top of the wall. This would actually place it above the concrete foundation. But on the outside, I'd have to cut through hardiplank. On the inside it would just be drywall and studs.
Since it's load-bearing - I'll have to put a header in. Can't think of a reasonable way to do that without removing the siding. But I hate to remove the siding - I'll never find paint to match.
In a perfect world, I could just cut a hole exactly the side of the new windows and slide it in, caulk it up and be done (yeah right).
You frame out the support from the inside, not the outside. The issue will be flashing the unit properly without removing the siding. You can get a drip cap in place with the siding intact and caulk the perimeter, but this is not the best way to insure a weather tight installation.
You will still need to cut through the siding to precisely fit the window.
The paint issue shouldn't be one. If you have to paint the side of the house, paint it.