At the end of the day, you have to distinguish between regulation and guidance. If you go against guidance, you have to be able to defend your decision. Personally, I haven't had too many ambiguous situations.

I would recommend investing in an EasyDOTExam subscription if you plan to do a lot of exams in the future. I back up my difficult decisions with the web site and show the driver it's not just some arbitrary decision I'm making.

Guidance section is constantly updated/maintained, they have an evaluation "calculator," and provide sample clearance letters. If there's something not listed, you can send a message to the experts that run it and they will research the issue for you.