Ultra-cool dwarf stars are abundant, long-lived, and uniquely suited to enable the atmospheric study of transiting terrestrial companions with JWST. Amongst them, the most prominent is the M8.5V star TRAPPIST-1 and its seven planets. While JWST Cycle 1 observations have started to yield preliminary insights into the planets, they have also revealed that their atmospheric exploration requires a better understanding of their host star. Here, we propose a roadmap to characterize the TRAPPIST-1 system -- and others like it -- in an efficient and robust manner. We notably recommend that -- although more challenging to schedule -- multi-transit windows be prioritized to mitigate the effects of stellar activity and gather up to twice more transits per JWST hour spent. We conclude that, for such systems, planets cannot be studied in isolation by small programs, but rather need large-scale, jointly space- and ground-based initiatives to fully exploit the capabilities of JWST for the exploration of terrestrial planets.