I'm wondering if complimenting a woman's looks could work if you are in a profession where you might be seen as a good judge of it..
For example a model photographer? Thoughts?
Yes of course. This is why these rules are kind of silly. They're meant for guys unplugging. A lot of guys on this thread are high value men, so they shouldn't be afraid to dispense with a compliment when it's coming from a place of high value.
Obviously a photographer, if he's high value and knows it, will throw out a compliment or two because 1) he's directing the photoshoot and he can (status), 2) he needs his subject to relax and feel good about herself, so it's in his interest, and 3) (optional) because he means it.
He's not complimenting her because he hopes it will get into her pants. And really most professionals probably want to avoid this kind of reputation, but that's another thread.
And as others mentioned it's how you say it. If he says "Gosh you're pretty" like a chump it will be worthless. But if he says "that green dress is really going to bring out those eyes in this photo," or "you're going to break a lot of hearts on Instagram next week," well, I think you can see the difference in effect.
Rules of discretion and restraint are great for guys starting out. If you're successful and high value, you can toss out the rulebook as long as you remember the fundamentals. A compliment from YOU at the right time and place is worth 1,000 "likes" or chump compliments.