We report parallax measurements for 70 ultracool dwarfs (UCDs). Using both literature values and our sample, we report new polynomial relations between spectral type and M$_{JHK}$. Including resolved L/T transition binaries in the relations, we find no reason to differentiate between a "bright" (unresolved binary) and "faint" (single source) sample across the L/T boundary. Isolating early T dwarfs, we find that the brightening of T0-T4 sources is prominent in M$_{J}$ where there is a [1.2 - 1.4] magnitude difference. A similar yet dampened brightening of [0.3 - 0.5] magnitude happens at M$_{H}$ and a plateau or dimming of [-0.2 - -0.3] magnitude is seen in M$_{K}$. Comparing with evolutionary models that vary gravity, metallicity, and cloud thickness we find that a near constant temperature of 1200 $±$100 K along a narrow spectral subtype of T0-T4 is required to account for the brightening and color magnitude diagram of the L-dwarf/T-dwarf transition. Furthermore, there is a significant population of both L and T dwarfs which are red or potentially "ultra-cloudy" compared to the models, many of which are known to be young indicating a correlation between enhanced photospheric dust and youth. For the low surface-gravity or young companion L dwarfs we find that 8 out of 10 are at least [0.2-1.0] magnitude underluminous in M$_{JH}$ and/or M$_{K}$ compared to equivalent spectral type objects. We speculate that this is a consequence of increased dust opacity and conclude that low-surface gravity L dwarfs require a completely new spectral-type/absolute magnitude polynomial for analysis. ; Comment: 65 pages, Accepted for publication to ApJ