The Kepler mission has enabled new science based on the demographics of exoplanets, including the investigation of the provenance of the observed transit multiplicity around Sun-like stars. Using just the Kepler observed transit multiplicity, we constrain whether and for how long the orbital architectures of planetary systems around FGK dwarfs dynamically evolve. These constraints will provide an upper runtime bound on expensive N-body simulations for orbital evolution, as well as a lower bound for the time at which life might emerge in systems around stars similar to the Sun. Yet, despite the bounty of planets from Kepler and TESS, follow-up for mass constraints and other characterization continues to be a precious resource. I will show preliminary results from an information theory-based approach to optimizing strategies for radial velocity follow-up observations of TESS planet-hosting systems.