Having enjoyed infinite jest, I was looking for comparisons trying to determine if I could make it through GR as well. Reddit says Gravity's Rainbow makes infinite jest look like twilight in comparison...
I posted about it above, but I tried to read Gravity's Rainbow right after Infinite Jest. While the latter was a bit confusing to follow early on, once you make sense of characters, it's pretty easy to keep going. The writing was fairly straightforward (even including the million side notes). I cannot say the same for GR. I gave up a third to a quarter in, having realized that I have no idea what's going on and that I can only follow the story line based on the Wikipedia summary. It definitely felt like a different level of convoluted compared to IJ.
I think you may have dropped GR right when it started to pick up a thread. You have to be willing to page back here and there when you pick up a reference you think you heard earlier to get clarity, but I had this with IJ too.
Trust me, GR really starts to flow and becomes really funny. It’s literature crafted at a super high level of skill.
I guess my point is you start to follow certain characters, certain other ones pop up again and again, and some come and go. It isn’t unusual to page back and reread a bit to refresh. But it really becomes a page turner eventually.
I never yet to read Gravity's Rainbow, but I did read Pynchon's first novel V as well as Infinite Jest.
Infinite Jest is much more approachable in my estimation than V, which I understand is itself more approachable than Gravity's Rainbow.
Aside the foot note gimmick, Infinite Jest is pretty easy to follow. The difficulty as such is mostly just the length.
I like DFW quite a bit, but I think Pynchon is the better author. So far I just haven't managed to start Gravity's Rainbow, I was scared off by the hype.