Also this isn’t exactly what you’re getting from Readwise, but you might also find these two things of interest:
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I have a couple of shortcuts on iOS that open random files in specific databases/groups. I run one daily. (This doesn’t work on Mac)
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I have some smart groups on MacOS that show me files that haven’t been interacted with in specific timeframes. It’s not a perfect system, because DT on Mac doesn’t know what files you’ve opened in DTTG, and as I read in iPad DTTG mostly I get a lot of false positives. However, it does mean that I am resurfacing content and not just losing stuff in my database. (Smart groups don’t work on DTTG so be aware that this is a task for your Mac).