Freeing Up Memory
Would it be wise to free up context now or should we continue as is?

Freeing up context now is the wise move — and this is precisely the right seam to do it. Honest assessment of where we stand: this conversation is long enough that the system has already been trimming older tool results (the original GitHub fetches are gone from my working context; I'm operating from the files we generated)... The one thing a fresh session lacks is our accumulated decisions — so the move is to write those down now, while I still hold all of them, as a handoff document.