Maximum always seems to be 5k points, played two rounds on Hard and Medium. Hard is a bit goofy because you might just look at a hill roadside and that's pretty generic in GTA. Closest was 2m. Worst 1200m in the hills. I actually think there is no real place that I know as well as Los Santos, and I haven't even played GTAV for years.
Real places are more difficult because they change over time. And some of them seem just as full of seemingly copy/pasted objects as the games... (or worse? Games have come a long way since the ubiquitous crate, on the level of production standards of GTA they probably go deep on generative variations)