In computer security, shoulder surfing refers to using direct observation techniques, such as looking over someone's shoulder, to get information. It is commonly used to obtain passwords, PINs, security codes, and similar data. Wikipedia
in loco Santaclausis
A play on the Latin phrase "in loco parentis," which means "in the place of a parent" and refers to the legal responsibility of an organization (e.g., a university) to take on some of the functions and responsibilities of a parent.
friends who warbike around town
Warbiking is, in Internet vernacular, searching for unsecured wireless networks by bicycle. 
Daytona [...] suspends here comical-Negro shtick for a minute
So is Daytona black or not? Up to this point, it seemed she was, but perhaps not? More of that Pynchon ambiguity...
All About Eve and shit
The 1950 film is about a successful actress and her young fan Eve Harrington, who insinuates herself into the older actress's life.
Out there somewhere in that nomad's field of indifference, riding the Chinese bus into a futurity of imprecise schedules and reduced options
This is reminiscent of the fate of Tyrone Slothrop, in Gravity's Rainbow, pages 738-742 (original Viking editions), where he is "scattered" and eventually sort of disappears from the action, dissolves.
Like Slothrop, Windust:
He's silent, wherever he is. One more American sheep the shepherds have temporarily lost track of, somewhere in the high country of this ruinous hour, cragfast in the storm.
a pair of fishhooks
"Fishhook" is gambling lingo for a Jack of any suit.
a music track heavy on the hijaz scale
The hijaz scale aka the Phrygian Dominant, Hijaz-Nahawand, Fraigish is distinguished by the augmented interval between the 2nd and 3rd degrees of the scale, which is commonly heard in Jewish, Greek, Turkish, Arab, Persian, and Flamenco music. The scale is: D Eb F# G A Bb C. Wikipedia
his careless gift of boy's cruelty
A "careless" gift is a meaningless gift given with little thought. It's Windust giving the Montauk Project his gift of "boy's cruelty" which was nurtured and developed. See page 339 Windust would be "a preadolescent boy [...] abducted circa 1960" by the Montauk Project, as described on page 243.