Speaking as someone from Edinburgh where the locals are notoriously jaded (ask someone that has lived in edi for a few years what festival shows they went to this year): It's more that we _forget_ rather than never knowing.
Asks me what cool things to do nearby on the spot and I'll probably draw a blank. But say what you are doing instead and I'll probably go "oh yeah! That's brilliant! I love thing X".
I do know where good dog walking spots just outside Edinburgh are though, and I'm still regularly discovering more because I'm effectively a tourist ;).
I struggle with this too in Edinburgh; I make a point of trying to stay engaged and keep recognizing how amazing the place is from the outside.
Going to the festival (and the book festival, back when that was in Charlotte Square) is improved by leaning into your local status and knowing how to duck in and out. And ideally knowing someone with a lanyard who can get you into the media bar: it's not cooler and more happening in there, it's actually quieter.
There's a vennel route across the city. It's an odd experience going through a deserted and mildly unpleasant alley, stepping out into a shuffling horde of tourists, cutting sideways across their paths, and ducking behind some bins into another quiet path. Like walking from the wings of the stage across it.