Given the very close proximity of their habitable zones, brown dwarfs (BDs) represent high-value targets in the search for nearby transiting habitable planets that may be suitable for follow-up occultation spectroscopy. In this paper, we develop search strategies to find habitable planets transiting BDs depending on their maximum habitable orbital period (PHZ out). Habitable planets with PHZ out shorter than the useful duration of a night (e.g., 8-10 hr) can be screened with 100% completeness from a single location and in a single night (near-IR). More luminous BDs require continuous monitoring for longer duration, e.g., from space or from a longitude-distributed network (one test scheduling achieved three telescopes, 13.5 contiguous hours). Using a simulated survey of the 21 closest known BDs (within 7 pc) we find that the probability of detecting at least one transiting habitable planet is between 4.5+5.6 -1.4% and 56+31 -13%, depending on our assumptions. We calculate that BDs within 5-10 pc are characterizable for potential biosignatures with a 6.5 m space telescope using ∼1% of a five-year mission's lifetime spread over a contiguous segment only one-fifth to one-tenth of this duration.