All contemplative soliloquies aside, your par-5 looks to be a replicate of the 17th hole at Pelican Hill North - although I am not sure whether Lester George knew he was copying Fazio, came up with the strategic geometry on his own or drew it up unconsciously.
I disagree that an experienced player or critic needs to play a hole multiple times to fully grok its intricacies. The trick (if that is what you want to call it) is take the time to start on the tee and walk the hole, taking careful note of how hazards and contours are arranged - because playing the hole in your mind from various spots is just as instructive as playing it with clubs.
When you get to the green complex, pay attention to the contours of putting surface and how the approaches are arranged for the aerial and ground game; now, you pretty much understand 90% of the author's intentions. The again I spent years riding in George Bahto’s sidecar . . . . .
One of the reasons I love to play an unfamiliar track with guys like Joel Stewart, Neal Meagher or Adam Clayman is nobody gives a shit what they shoot, but are firmly focused on dissecting the puzzle. What (competent) raters do is essentially reverse-engineer each hole in context with the flow of the golf course. I can no longer just ‘play", so unless we are walking down the fairway talking about football or pussy (to distract me), it is impossible to turn off the little camera and computer in my head.
I'm not sure that paintings are meant to be picked apart in the same way - but that might have more to do with the fact I like to contemplate most fine art as a singular expression. Of course, I have not a micron of talent with a paintbrush or pencil.
By contrast, I can safely be described as skilled in Cinematography - but long ago lost the ability to just watch a movie as a visual and dramatic presentation. My wife, who is an excellent editor, has somehow retained the ability to get into a film like a layman. I just sit there and make technical notes, mumbling to myself about lighting mismatches, cuts across the stage line and blown out windows - until I get a freckled elbow in the ribs and told to shut up.
From the standpoint of actually playing intricate golf holes like this par-5, I generally have no problem (on the cusp of dotage) figuring out my personal “line of charm.” Unless I’m faced with an obnoxious, uphill 450 yard Jack Nicklaus par-4, I can usually figure out a path to the next tee reasonably unscathed. It is ridiculously easy holes like #10 at Pacific Grove that beat me and eat me.
Like deceptively simple works of fine art, the more straightforward the hole, the harder it is for me to execute anything resembling a serviceable golf shot. I look for things that do not exist because it seems impossible that elegance can be expressed with such simplicity - in either golf architecture or art.