The vast abundance of low-mass stars makes their disks perhaps the most common sites for planet formation in our galaxy. Even so, constraining the frequency of exoplanets and the properties of disks around M-dwarfs and brown dwarfs remain open areas of active research. We present results from two investigations into disk evolution diagnostics for low-mass stars and brown dwarfs. The first of these involves ongoing efforts to constrain accretion and wind diagnostics for an ensemble of transition disk systems at the substellar boundary using high-resolution NIR spectroscopy with IRTF/iSHELL, illustrating the sensitivity required to detect very weak but persistent accretion signatures in low-mass disk systems. The second investigation is a multi-technique case study of the transition disk system V410 X-ray 6, classified as a 'giant-planet forming disk' around a young, low-mass object at the stellar/substellar boundary (?80 MJup). By combining (1) moderate-resolution NUV to NIR spectra to search for accretion and wind diagnostics as well as radial velocity signatures, (2) ALMA CO and continuum observations, and (3) previous high-spatial resolution observations using non-redundant masking interferometry, we examine the origins of the depleted gap in this system. The synthesis of these approaches highlight the utility of combining multiple observational techniques to assess evolutionary processes and the planet-forming environments within young, low-mass disk systems.