Mississauga handyman just uploaded a series of pictures up onto houzz.com this is a picture gallery website that displays many different pictures from different people.
In this particular series of pictures we were doing a quick and dirty paint job for customer for his daughter's wedding in the next few following days. He was planning to put in new windows next year but wasn't able to do the window replacements this year so he decided he would at least do some exterior painting on the front of his house here in Mississauga. These windows were probably somewhere around 5 to 8 years old and were only stained from the original builder. The staining is not a sealer and it allowed the water to penetrate through the wood making it dry out and rot.

The nice thing about staining wood is that most the time stain just fades away showing more and more of the bare wood and it is still easy to stand. Generally there are no flakes and paint peeling involved here it just looks bad and very weak.

The other problem with this situation was that all the caulking had dried out and cracked open. This allows all the rain to seep in behind the caulking soaking the wood from behind again ruining the integrity of the wood and window frame. That's why many times that the window sashes have to be replaced because it rot.

Problems with painting upper floor exterior windows is being able to place the extension ladder in the right place. Sometimes there is a problem with the placement of the legs/feet of the ladder if there is shrubbery in the way of where you want to place the ladder you might have a problem giving the latter to extend to the right position on the wall under or around the window.
Of course you don't want to put a ladder in the middle of a window and having the window support the weight of the painter leaning into the window off to top of the ladder. This could be a dangerous situation for both the painter and create damages to the window too much stress on the window frame might cause the window to crack. And you definitely do not want to place the ladder on the window pane itself. You are for sure looking for trouble here. In this situation the extension ladder was long enough to place it above the windows to be able to reach the middle of the window. And then both sides of the window were done leading the ladder up against the wall reaching into the window on opposite sides. Then we did the bottom of the window by leaning the ladder  on the wall in  basically center of the window.