Brown dwarfs and giant planets share many similarities in their physical properties and atmospheric dynamics, but the most fundamental difference between these two types of objects is the formation pathway that led to their creation. A key to differentiating between formation pathways might lie in their system architectures. Recent discoveries have unveiled a number of systems with substellar companions in orbital configurations that are challenging to directly attribute to a formation mechanism. These extreme systems are key pieces to understand substellar formation and its subsequent evolution as a population. In this talk, I will revisit the orbital properties of these systems, explore the parameter spaces that each distinct population occupies, and discuss the role of Gaia to identify signatures of top-down or bottom-up formation.