I think this and the weep hole being ineffective are more convincing.

His view is the water would have come form the 2nd level from the gap between brick and framing and find a weak point in the windows of 1st floor and entered the house. One in particular believed it has to do with gutter - whether they are sloped right, if one more down sprout is needed, and a portion of facia is loose. One pointed out the weep holes are all clogged up.

Most contractors look at the silicone seal around windows and flashing for loose gaps. I have called in 3 roofers, 2 G.Cs to advise the cost of repair and remedy and till now I am still uncertain about what caused this and who to call to get a definitive understanding of the root cause.

The exterior door in between the windows had water entering the wall and you can see stains around the door still. During Irma, my first floor's windows (north facing) about 8' on each side were leaking rainwater from the top of the window, similar to the manner of leaking in the video by Ada Lam above.

Windowtop crack