We present comprehensive orbital analyses and dynamical masses for the substellar companions Gl~229~B, Gl~758~B, HD~13724~B, HD~19467~B, HD~33632~Ab, and HD~72946~B. Our dynamical fits incorporate radial velocities, relative astrometry, and most importantly calibrated Hipparcos-Gaia EDR3 accelerations. For HD~33632~A and HD~72946 we perform three-body fits that account for their outer stellar companions. We present new relative astrometry of Gl~229~B with Keck/NIRC2, extending its observed baseline to 25 years. We obtain a $<$1% mass measurement of $71.4 pm 0.6,M_{rm Jup}$ for the first T dwarf Gl~229~B and a 1.2% mass measurement of its host star ($0.579 pm 0.007,M_{odot}$) that agrees with the high-mass-end of the M dwarf mass-luminosity relation. We perform a homogeneous analysis of the host stars ages and use them, along with the companions measured masses and luminosities, to test substellar evolutionary models. Gl~229~B is the most discrepant, as models predict that an object this massive cannot cool to such a low luminosity within a Hubble time, implying that it may be an unresolved binary. The other companions are generally consistent with models, except for HD~13724~B that has a host-star activity age 3.8$sigma$ older than its substellar cooling age. Examining our results in context with other mass-age-luminosity benchmarks, we find no trend with spectral type but instead note that younger or lower-mass brown dwarfs are over-luminous compared to models, while older or higher-mass brown dwarfs are under-luminous. The presented mass measurements for some companions are so precise that the stellar host ages, not the masses, limit the analysis.
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