Leaving a gap around windows and filling with caulking leads to disaster.

What makes things worse, the top of the window is angled back to the house. Note the standing water over the window. We took this video on a hot day and it hadn't rained in days.

A simple flashing over the window angled away from the house would have solved this, as long as there is no caulking over the flashing.

Andersen windows, who made the windows in the video, makes flashing for their windows. Here is Andersen window flashing we used in 2022. Andersen flashing can be ordered for the color of the window, and is correctly angled down, and shipped in cardboard mailing tubes.

Andersen window flashing is well made and has a nice kick on the edge for deflecting water. These are recommended for use when there is no trim over the window, which may require a different head flashing. If Toll Brothers and some of these other contractors read the instructions and spent a few bucks, this house wouldn't need extensive rot repaired. Of course, they put the drip edge on the roof backwards, also. Stupidity is a resource the world will never run out of.

Most of the houses in this area were done this way, and they almost all have had extensive repairs due to rot. Leaving a gap and filling with caulk is the road to rot. Besides, the caulking looks horrible. Caulking isn't made to be put on this thick and shrinks and cracks up. Also, the caulking is sticky and collects dirt. Note how badly this caulking is cracked up.