Exoplanetary science is a highly interdisciplinary field spanning planetary science, astronomy, and geophysics. This thesis presents a comprehensive exploration of exoplanetary science that combines these disciplines to investigate habitability in the context of diverse system architectures and planet sizes. Through interconnected studies, I demonstrate the power of multi-method approaches in discovering exoplanets and exploring the varied nature of exoplanetary systems, testing the boundaries of what can be considered a potentially habitable world.This thesis focuses on the detection and characterization of a wide range of system architectures, including different types of orbits, host stars, and planet sizes. Using transit photometry, radial velocity (RV) measurements, and astrometry I refine orbital parameters and discover planets in both new and known planetary systems. By applying these methods to the HD 9446, HD 43691, and HD 179079 systems, I illustrated the importance of long-term monitoring of planet systems in revealing system architectures. I refined the orbital solutions and transit ephemerides for these systems and discovered evidence of two possible additional long-period companions. Using a combination of RV and astrometry in my study of red giant star ι Draconis allowed me to refine the properties of a known eccentric planet and led to the discovery of a long-period companion on the planet/brown dwarf boundary. While such a massive object itself wouldn’t be considered habitable in the traditional sense, it could potentially host large moons. These moons, if they exist, could provide environments suitable for life, challenging our conventional definition of what constitutes a potentially habitable world and forcing us to broaden our search criteria when looking for places where life might exist. I combined TESS transit photometry and RVs to discover a Saturn-mass planet, TOI-1386 c, that also orbits partially within the HZ, and confirm the presence of a transiting warm sub-Saturn planet, TOI-1386 b. As TOI-1386 b is in the sub-Saturn mass regime this is an important addition to this demographic of planets due to the ongoing debate regarding the existence of the sub-Saturn gap.Further exploring the diverse system architectures that host potentially habitable worlds, I completed a comprehensive catalog of HZ exoplanets, compiling known planets that orbit within or through the HZ. I include the HZ boundaries, percentage of the orbit that each planet spends in their star’s HZ, and observational metrics for each planet such as TSM values and RV amplitude to facilitate selection for future follow-up observations. I highlight the extreme diversity of system environments that could challenge our traditional notions of habitability and call attention to some planets that would be ideal targets to test the boundaries of habitability. This catalog served as the boundary conditions for my final study where I built the Smaller Than Earth Habitability Model (STEHM).Using STEHM I tested the boundaries of habitability by exploring the lower size limit for potentially habitable planets. STEHM is a 1D model based on a thermal interior evolution and CO2 degassing model of a stagnant lid planet combined with a CO2 atmosphere loss module that varies according to the stellar flux received from a Sun-like star over time. By considering various factors, such how internal heat generation, carbon degassing and atmosphere loss changes with the size of the planet, STEHM provides crucial insights for future exoplanet exploration missions and expands our understanding of planetary habitability.As we improve our ability to detect and characterize planets, we uncover an incredible diversity of worlds with different architectures and sizes of planets both in and around the HZ. The techniques and insights presented here will guide the next generation of exoplanet studies of these potentially habitable worlds. Our detection work provides insight into these planetary system architectures, the HZ catalog provides a selection of targets that can serve as the ideal test cases for planetary habitability and our model results from STEHM can be directly applied to future James Webb Space Telescope and HabitableWorlds Observatory observations of smaller than Earth sized planets to help determine their habitability.