I do something similar - as I approach the context limits I have a pre-compact flush skill that extracts anything useful from the context, updates the MEMORY.md and my Obsidian vaults (set up as a poor man's graph DB) and so forth. Once everything's been stored I run /compact to keep the general session flow intact. Recently I added a small embedder/vector search setup to the same skill, which seems promising so far.

On another environment I've been doing something roughly similar, but have integrated Hindsight as a kind of all-in-one of the above and am still trying to suss out the best compaction strategy.