Agree about the dog.No. It's very black and white spelled out in countless flying articles on the topics and backed up by FAA interpretations. There's been literally no subjectivity to this as long as I've been flying.
Also, FSDOs don't interpret regulations. Following regulation interpretation from FSDOs is like getting legal advice from your dog.
But actually, there was an "off" FSDO interpretation maybe 25 years ago, which followed the most common misunderstanding.
The Buffalo FSDO published a statement on their website that every leg had to be more than 50 NM long. IOW, every "point of landing" had to be >50 NM from the previous takeoff. There was a short letter-writing campaign and the posting disappeared in about two weeks.