The thing that makes Pynchon worth re-reading over and over again is that while the intention of his firehose of psychedelic bullshit is to bewilder you and induce a state of mind that approximates taking a psychedelic... (almost :P) every single piece of what he does is extremely interesting.

This creates a situation where the first time (or like... the second or third hahaha) of reading a Pynchon novel can be like a weird dream where random shit happens, but eventually you will have an experience where something you assumed Pynchon made up as some stupid gag or joke is actually terrifyingly real or a strikingly beautiful metaphor that precisely captures something bizzarely specific and technical, and reality will feel inverted on you, and that is the moment you will realize Pynchon has put his hooks in you.

I guess what I am trying to say is that if you read Gravity's Rainbow and vibe with it, you don't have to keep pursuing meaning in the book or enjoyment, it will start ambushing you in the rest of your life as you realize Pynchon despite being crude and annoying and extreeeeemely verbose (as am I, sorry) is pointing directly at the crucial unspoken conversations and realities at the heart of what is driving the world apart.

Gravity's Rainbow is in many ways barely about WW2 from the perspective of what you would define traditionally as a work of historical fiction about WW2 (though Gravity's Rainbow has extensive references to history involved in WW2, people have written books about it) but the heart of it, or hearts of it, are so fucking damn good that I consider it the only actual WW2 novel I have ever read besides maybe Catch-22, and Gravity's Rainbow blows that book out of the water purely on a basis of density of interesting ideas launched at you in salvos in every Pynchon paragraph/sentence.

Also, try Inherent Vice! Then watch the movie!