Choose the deployment boundary
A desktop utility, a command-line tool and a server process have different needs. Decide whether the user can install Python, whether updates are frequent and how failures will be diagnosed.
Compare real trade-offs
Single-file bundles are convenient but can be large and opaque. Native installers improve integration. Containers fit controlled infrastructure. Standard packages remain the most transparent option for technical users.
Test the artifact, not just the source
Build on clean machines, verify missing-runtime behavior and keep a reproducible manifest of dependencies. A packaging workflow is complete only when the produced artifact is exercised end to end.