Poor roof / building design

This was a new build in Florida. This area of the roof / wall intersections will need constant monitoring for the following: filling with debris, damage and water intrusion from rainwater being directed and channeled against the block wall. One piece of kick-out flashing does not constitute complete and proper flashing in this area. Recommended the clients get a second opinion from a qualified roofer as to the need for improved sidewall and headwall flashing in this area.

That is screwed up.

There’s about a million of those (exactly the same) dead-valleys in our area.
Many leak, many don’t.

Still a piss poor design. 50/50 odds that it won’t leak is not an acceptable design.

I put the blame squarely on architects, they design crap that looks good on paper without considering the dynamics or the building science.

You should see the number of “MacGyver repairs” to these roof/wall intersections I have seen over the years. Even properly flashed they stand a good chance of failing.

I strongly agree on that. Seen it more than once. But in those instances I would tell them in there face it is screwed up and for them to look into it before I built it. Usually, it worked.