Two quick questions:
1. Are your links mostly local files, web URLs, or a mix? 2. When you say “end up in those places again”, do you want it to save a trail/session automatically (like a breadcrumb graph), or just learn “these links co-occur with this query” over time?
I’m exploring a similar “context neighborhood” retrieval loop (more context in my HN profile/bio if you want to compare notes).