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"Bleeding Edge" has a number of meanings. See Bleeding Edge Title. The phrase first appears on pg. 78 "What's known as bleeding-edge technology. [...] No proven use, high risk, something only early-adoption addicts feel comfortable with."
The cover photograph is of a server farm. I found it here. It's entitled "Server Farm at Night." Note how the image also evokes the World Trade Center, and the cover of Pynchon's V. ...
More info at Bleeding Edge cover analysis
Book jacket description
Pynchon likely wrote the copy for the book jacket description of Bleeding Edge and he likely did the same for Inherent Vice.
This Westlake quote is in a New York Times article, dated October 31, 1999, about New York City. In the article, credit is given thus: "Tucker Coe (a.k.a. Donald E. Westlake writing about a cop, a brick wall and guilt. Out of print.)." So it's most likely from Westlake's (writing as Tucker Coe) "Mitch Tobin" series.
From Westlake's Wikipedia entry:
- Tucker Coe: 5 mystery novels featuring the character of Mitch Tobin: Kinds of Love, 'Kinds of Death, 1966; Murder Among Children, 1967; Wax Apple and A Jade in Aries, both 1970; Don't Lie to Me, 1972.
From this website:
- Donald Westlake adopted the pseudonym Tucker Coe for a series of five superb novels about guilt-ridden ex-cop Mitch Tobin, thrown off the NYPD after his partner was killed while Tobin was spending duty time enjoying the adulterous bed of a lady whose husband was in prison. Tobin's wife forgave the infidelity, but Tobin couldn't forgive himself. He spent his time in the backyard, slowly building a brick wall to keep out a world he no longer believed he had a place in. He supported himself and his family by taking on occasional investigations, but he does so with great reluctance. Slowly, though, the casework had the therapeutic effect of forcing him to come to terms with his guilt and deal with it. Tobin was introduced in Kinds of Love, Kinds of Death (Random, 1966). By his last appearance, Don't Lie to Me (Random, 1972), Tobin had obtained a P.I. license (thus making himself no longer eligible for consideration in this column), gotten a part-time job as a night security guard at an art museum, and was well on the way to psychological recovery. Largely on the strength of the Tobin series, Westlake was awarded the P.W.A. “Eye” award for Lifetime Achievement as a private eye writer.
Donald Westlake (1933-2008) was an American writer, with over a hundred novels and non-fiction books to his credit. He specialized in crime fiction, especially comic capers, with an occasional foray into science fiction or other genres.
In the below video (at :58), Donald Westlake refers to an "article" where one of the questions being asked was: "If New York City itself were a character itself in a mystery novel, what would that character be? And I said it wouldn't be the detective, because the detective cares who killed, and NY doesn't care. And it wouldn't be the murderer because the murderer has to care about someone he kills. So I think the character New York would be would be the enigmatic blond who knows the answer but isn't going to tell you."
The title page feature a photograph of the Flatiron Building, a skyscraper in NYC. "The neighborhood around it is called the Flatiron District after its signature building, which has become an icon of New York City." Wikipedia
Like Inherent Vice and Against the Day, Bleeding Edge has no dedication. Pynchon dedicated three of his earlier novels to friends and family: Mason & Dixon ("For Melanie, and for Jackson"), Vineland ("For my mother and father"), and Gravity's Rainbow ("For Richard Fariña").
"the first day of spring, 2001"
three instances of beginnings: the first day, of spring (the season of beginning and renewal), of the new millennium.
"though some still have her in their system"
the novel's first sentence invokes the topic of personal data held in various databases or systems.
Literally translated from German, it means 'someone who eats with a spoon'. It is not an uncommon last name in Germany; it is also the German name of a bird, the Eurasian Spoonbill. Wikipedia
Loeffler is also the name of a German composer, Charles Martin Loeffler. Very interesting to note that the composer's father wrote journalism under the name 'Tornov' or 'Tornow' while the son sometimes used it as a middle name. 
"walking her boys to school"
This scene -- a parent walking children to school in the Upper West Side of New York City -- is, more than any of Pynchon's novels, evocative of what is reported of Pynchon's biography.
- This could be an early hint that the novel has a more autobiographical element than any of his previous works? Benvolio (talk)
Callery Pear trees
Planted extensively in NYC due to its fast-growing nature and tolerance of pollution and other extreme conditions. Central Park Conservancy Their blooming is a first sign of spring.
- Much has been written on how Callery trees smell like semen. E.g., article
she drifts into a pick
A "pick" is a basketball term. It refers to an offensive player blocking a defensive player.
a term meaning those homeless who sleep in such places as doorways and lobbies. "The word unhoused refers to that segment of a homeless community who do not have ordinary lawful access to buildings in which to sleep, as referred to in the HUD [United States Department of Housing and Urban Development] definition as persons occupying "place not designed for ... sleeping accommodation for human beings." "Wikipedia
- added thought: Pynchon has tickled his creatures with Heideggerian thought throughout his writing. Unsheltered is not the "normal" way in which we describe our "homeless".
- I'd contest the interpretation of "unsheltered" as somehow related to Heidegger. All of Pynchon's novels feature specialized language, e.g. military, scientific, accounting, law. The use of "unsheltered", a word used by professionals dealing with homeless people, can more readily be read as simply one more example of that. Benvolio (talk)
a popular brand of scooter, but note how the word "razor" echoes/evokes the title, Bleeding Edge.
A fictitious character, i.e. no real person. Maybe Otto Rank  was the blueprint for Otto Kugelblitz.
German, "ball lightning". The Kugelblitz was also the name of a tank in WWII. Wikipedia
- Many references to Germany, German words, names and German history run throughout Pynchon's oeuvre, to the point where Pynchon scholar David Cowart posits that "Pynchon seems to have had a German period, a post-German period, and a neo-Continental or global period. During his German phase he produced his first three novels... His next work, the long-awaited Vineland, represents a new phase in which the almost obsessive attention to German more seems to have faded." Thomas Pynchon and the Dark Passages of History (2012), at p. 59. Benvolio (talk)
- A character name Skip the sentient ball lightning appears in Against the Day. 
the human life span runs through varieties of mental disorder as understood in his day- the solipsism of infancy, the sexual hysterias of adolescence and enty-level adulthood, the paranoia of middle age, the dementia of late life... all working up to death, which at last turns out to be "sanity"
This theory may of further importance, i.e. could it be a kind of program for this novel?
Solipsism > sexual hysteria > paranoia > dementia > deatch > sanity
on a cross street Law & Order has so far managed not to film on
Law & Order was the longest running crime drama on TV. It ran for 20 seasons and filmed its episodes on the streets of New York City. Of course, this adds to building sense of paranoia and fear in this opening description.
The address in Vienna where Freud lived. It is now the site of the Sigmund Freud Museum.
The name sounds like the German word "Wirrwarr", meaning something like "muddle", "huddle", etc.
Vyrva speaks in uptalk, or phrasing statements like questions, a linguistic characteristic found (among other places) in Southern California, especially among so-called "Valley girls". Wikipedia
Pomona College, a prestigious, private liberal arts college in Southern California
real-estate envy attack
A combination of penis envy, which is one of Freud's theories, and a heart attack.
Maxine runs a small fraud-investigation agency
"Fraud" sounds quite similar to the name of the psychologist "Freud" who was mentioned on the previous pages. So is Maxine perhaps a "Freud-investigator"?
antennas for the unspoken
Cf, a letter by Pynchon: "Given the British genius for coded utterance, this could all be about something else entirely, impossible on this side of the ocean to appreciate in any nuanced way..." Source
Also brings to mind Inherent Vice's protagonist, who claims "if acid tripping was good for anything, it helped tune you to different unlisted frequencies." (62) Another person whose profession affords them a kind of social ESP, it seems.
a dating service called Yenta Expresso
Yenta is a Yiddish loanword which generally means a busybody or someone who spreads gossip. Given that it's seen in the name of a dating service, it's likely a reference to the musical/film Fiddler on the Roof, where the village matchmaker's name is Yenta. Y'know, it's a shame real life could never be as hyper-referential as Pynchon's reality.
Krispy Kreme is set to go public on NASDAQ only days from Maxine's message, and ironically centering around a company whose intellectual property (the recipes!) were bought and not developed. .
the gates of Danbury
a federal prison. Wikipedia
American electronics store famous for its radio and TV ads in the 60s and 70s, featuring the slogan, "his prices are insane". The T-shirt in question was designed by, of all people, Robert Crumb. The TV ads featured New York disc jockey Jerry Carroll as the pitchman. Wikipedia
"Crazy Eddie" also features prominently in the science fiction novel The Mote In God's Eye by Larry Niven and Jerry Pournelle (1974), signifying both an archetype of insane optimism and a spatial gateway for interdimensional travel.
as Britney always sez
"Oops! I Did It Again" was a huge pop hit in 2000 for Britney Spears.
"Help Me Rhonda"
1965 song by the Beach Boys. Pynchon reportedly recommended that Jules Siegel listen to the Beach Boys' Pet Sounds, as recounted in Siegel's article, "Who is Thomas Pynchon, and Why Did He Take Off With My Wife" (1977). Pynchon mentions "Help Me Rhonda" and two other Beach Boys hits in Inherent Vice.