This looks like a “racked” installation. Pull up the manufacturer’s install instructions to see if it is allowed. Generally speaking it is a “less reliable” way to install asphalt shingles.
The orientation is fine, but the location of the “cut” is suspect in my opinion. Appears to be facing uphill.
Like Ryan said, first image looks racked. However, I believe I see 5 or so shingle ends on picture #2, and they didn’t appear to be racked.
Racked installation is more a warranty issue. I’ve never seen leakage. As a carpenter, I used to shingle that way for a while, meaning I own quite a few warranties. IMO, it’s mostly an issue of not following manufacturer installation instructions (which I was guilty of, not reading the printed information present on each pack of shingles). GAF Timberline is not manufacturer approved for racked installation.
I wouldn’t write very hard on either the racked or woven valley issues. Loss of warranty (as useless as it is) is one issue to point out.
Rarely does a racked installation cause trouble because the main function of the shingles is to protect the underlayment. But your photos show one of the several weaknesses of drone inspections. When we can get on a roof, we should.