Underrated the original vs the remake — am I overthinking this? [v5]

Mostly thinking out loud — feel free to push back hard. Spent the last few weekends digging into this and the deeper I go the more questions I have. Quick context: I am relatively new to this and trying to find my footing.

Not sure if this is the right place to ask, mods please remove if it is not. The trade-offs here are not obvious to me and I keep flip-flopping.