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Benchmark systems are critical to assisting sub-stellar physics. While the known population of benchmarks has increased significantly in recent years, large portions of the age-metallicity parameter space remain unexplored. Gaia will expand enormously the pool of well characterized primary stars, and our simulations show that we could potentially have access to more than 6000 benchmark systems out to 300 pc, allowing us to whittle down thesenbsp;systems into a large sample with outlier properties that will reveal the nature of ultra-cool dwarfs in rare parameternbsp;space. In this contribution we present the preliminary results from our effort to identify and characterize ultra-coolnbsp;companions to Gaia-imaged stars with unusual values of metallicity. Since these systems are intrinsically rare, wenbsp;expand the volume probed by targeting faint, low-proper motion systems.nbsp;/p>