Okay, I finally gave this a watch the other night. Bear in mind that this was my first viewing of either film, I’ve never seen the Tim Curry version, and I only read the book once, years and years ago (and can’t remember if I finished it).
Overall, I really liked it and feel like the studio’s choice to split the story up by era probably severely harmed it, especially part two, since the older Losers’ story exists primarily as a framing device for the younger Losers’ story until the ending, and splitting that off on its own can’t have worked very well.
However, this edit isn’t totally seamless. I didn’t take specific notes or anything and don’t know if I’ll revisit your cut anytime soon to do so, but here are my general thoughts:
The biggest issue I have is that it often didn’t feel like there was much rhyme or reason to tie together the “flashbacks.” We’d get a bit of 2016 material, then it would flash back to 1989, but it didn’t feel like a natural progression, like “this is what Richie is remembering” Instead it was more, “Richie is remembering something, now here’s 30 minutes of the kids, 15 of which don’t involve Richie at all.”
Then there are things that are shown out of order/context that were confusing, like when Bowers is arrested by the cops but keeps showing up in the 1989 timeline. I assumed I’d missed a scene where he escaped from jail or something, but by the end I realized that it apparently took place after the Losers’ 1989 battle with IT. The structure is already nonlinear, so as much as is possible, the 1989 and 2016 stories should both proceed linearly in parallel unless there’s a good reason not to.
Finally, there was a lot of inconsistency in how the switching between timeframes happened - sometimes it was a dip to white, sometimes it was an organic transition that I can only assume was as it’s presented in the second movie, sometimes it was just a cut. These should be made as consistent as possible, if at all possible.
I’m also not a fan of putting fan edit titles over actual title screens, but that’s a personal nitpick.
NOW, I don’t want you to think I’m just shitting all over your edit - it was very well done for a first edit, and I absolutely know I enjoyed this far more than I would have enjoyed watching each film individually, I just think there’s room to make it even better!