Abstract We present the full results of our decade-long astrometric monitoring programs targeting 31 ultracool binaries with component spectral types M7–T5. Joint analysis of resolved imaging from Keck Observatory and Hubble Space Telescope and unresolved astrometry from CFHT/WIRCam yields parallactic distances for all systems, robust orbit determinations for 23 systems, and photocenter orbits for 19 systems. As a result, we measure 38 precise individual masses spanning 30–115 . We determine a model-independent substellar boundary that is ≈70 in mass (≈L4 in spectral type), and we validate Baraffe et al. evolutionary model predictions for the lithium-depletion boundary (60 at field ages). Assuming each binary is coeval, we test models of the substellar mass–luminosity relation and find that in the L/T transition, only the Saumon & Marley “hybrid” models accounting for cloud clearing match our data. We derive a precise, mass-calibrated spectral type–effective temperature relation covering 1100–2800 K. Our masses enable a novel direct determination of the age distribution of field brown dwarfs spanning L4–T5 and 30–70 . We determine a median age of 1.3 Gyr, and our population synthesis modeling indicates our sample is consistent with a constant star formation history modulated by dynamical heating in the Galactic disk. We discover two triple-brown-dwarf systems, the first with directly measured masses and eccentricities. We examine the eccentricity distribution, carefully considering biases and completeness, and find that low-eccentricity orbits are significantly more common among ultracool binaries than solar-type binaries, possibly indicating the early influence of long-lived dissipative gas disks. Overall, this work represents a major advance in the empirical view of very low-mass stars and brown dwarfs.