Multiplicity is one of the foremost diagnostics for the formation processes of brown dwarfs, and thus low-mass substellar binaries lie at the nexus of astronomical interests, representing the youngest products of star formation at the very lowest masses, and at the same time serve as analogues to directly imaged giant planets. Due to the lack of a statistical significant sample readily available, multiplicity is poorly constrained at the lowest stellar and substellar mass-regimes, which in turn has consequences for theoretical evolutionary models to fail to accurately predict masses from measured luminosities. By monitoring visual low-mass binaries over longer periods of time, applying precise astrometry, and employing high-contrast imaging techniques, we are able to identify and characterize several new benchmark binary and higher hierarchical systems, constraining their ages, brightnesses and masses, which can be used to calibrate said evolutionary models. The detection of these systems also allow us place constraints on the multiplicity frequency for young brown dwarfs, which compared to the older field population provides insight to their formation mechanisms and dynamical evolution.