"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."
More info at Bleeding Edge cover analysis
Book jacket description
Donald Edwin Westlake (July 12, 1933 – December 31, 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. He was a three-time Edgar Award winner, one of only three writers (the others are Joe Gores and William L. DeAndrea) to win Edgars in three different categories (1968, Best Novel, God Save the Mark; 1990, Best Short Story, "Too Many Crooks"; 1991, Best Motion Picture Screenplay, The Grifters). In 1993, the Mystery Writers of America named Westlake a Grand Master, the highest honor bestowed by the society. More on Wikipedia
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.
"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
- Much has been written on how Callery trees smell like semen. E.g., article
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
a popular brand of scooter, but note how the word "razor" echoes/evokes the title, Bleeding Edge.