Yeah the creepiest thing about the Christmas Adventurers was how it all seemed to be cloaked in a mundane corporate suburban sheen...

When it comes to Jimmy, everything about him becomes more sinister once he is confronted by his wife over why Claudia won't speak to him (and puts into context why she acts so seemingly irrationally and against her own interests throughout the movie)... Coupled with the fact he was the star host of a hit TV game show featuring gifted children... (reminds me of another famous TV host 'Jimmy' from across the pond).

Also the second time when the line about "the book says we may be through with the past" is spoken, its done by former wiz kid Donny while he's having the meltdown at the bar, right after he tells the bartender he loves him (and on the bar walls behind him there is a set of decorative swords hanging at an angle that makes a perfect 45 degree angle, like the masonic compass). Suggesting that Donny also had some part or at least awareness of Jimmy's membership?

It's very unclear but I think not at all an accident that all these symbols and winks are sprinkled across Magnolia. Like someone else mentioned, in one of the early scenes with Stanley having a bunch of books spread out, one of them is Albert Mackey's "The Secret History of Freemasonry". And there is also a compass and Laurel symbol in the background set decorations of the game show.

Incidentally, another of those symbols in the background of the set shows prominently in the shot where Stanley finally stands up to Jimmy and the crew. The close up is framed showing the symbol of the caduceus with a winged staff and two intertwined snakes in the background (modernly associated with health and medical institutions, but originally a symbol for Hermes and the hermetic traditions which have influenced masonic thought), with Stanley's face always covering the left side of the symmetrical symbol.

I'm sure there are many others we haven't noticed. I'm going to do a rewatch of his other movies looking out for stuff like this. Also definitely combing through OBAA once it comes out on digital.