For anyone wondering about Pynchon, I can say that The Crying of Lot 49 I did find approachable and it has made quite a lasting impression. It's not too long or too dense. And you may find a reference or two that have been subsumed by our greater culture. (As an example, I understood the reference when I saw Radiohead's fan club was called W.A.S.T.E..)
Gravity’s Rainbow, V and Against the Day are these monumental books which are sometimes really harrowing and hard to read (amazing in my opinion, but tough to read none the less).
Lot 49, Inherent Vice, Vineland and the new one are kind of “weird noir” gumshoe novels - funny and full of whacky conspiracies etc.
Bleeding edge is more like the second lot. I would definitely recommend people to read The Crying of Lot 49 and/or Inherent Vice to make up their minds whether they like Pynchon. Then you’ll know whether you want to invest in reading V or Gravity’s Rainbow etc.
[1] I’m gonna leave Mason & Dixon to one side because it’s sort of its own thing.
I also liked Crying of Lot 49. Inherent Vice is also a bit of an easier time.
Having said that, check out the illustrated "Pictures Showing What Happens on Each Page of Thomas Pynchon's Novel Gravity's Rainbow."
Against the Day is life changing.