SkyPortal is an open-source software package designed to efficiently discover interesting transients, manage follow-up, perform characterization, and visualize the results. By enabling fast access to archival and catalog data, cross-matching heterogeneous data streams, and the triggering and monitoring of on-demand observations for further characterization, a SkyPortal-based platform has been operating at scale for 2 yr for the Zwicky Transient Facility Phase II community, with hundreds of users, containing tens of millions of time-domain sources, interacting with dozens of telescopes, and enabling community reporting. While SkyPortal emphasizes rich user experiences (UX) across common frontend workflows, recognizing that scientific inquiry is increasingly performed programmatically, SkyPortal also surfaces an extensive and well-documented API system. From backend and frontend software to data science analysis tools and visualization frameworks, the SkyPortal design emphasizes the re-use and leveraging of best-in-class approaches, with a strong extensibility ethos. For instance, SkyPortal now leverages ChatGPT large-language models (LLMs) to automatically generate and surface source-level human-readable summaries. With the imminent re-start of the next-generation of gravitational wave detectors, SkyPortal now also includes dedicated multi-messenger features addressing the requirements of rapid multi-messenger follow-up: multi-telescope management, team/group organizing interfaces, and cross-matching of multi-messenger data streams with time-domain optical surveys, with interfaces sufficiently intuitive for the newcomers to the field. (abridged)