Cross-Platform Installer & Licensing System

I need my existing on-prem application turned into a downloadable installer for Windows, macOS, and Linux. Once a user signs up on my site and pays or redeems a promo code, they must automatically receive an email containing their personal license and the correct download link.

The installer should embed its own tracking so I can see activations, usage patterns, and uptime or downtime events without relying on third-party analytics. I also need an outage-alert dashboard fed directly from this data.

Patch management is equally important: when I publish a new build, the app should compare versions, download the update, and apply it with minimal user friction while preserving their license. A simple versioning scheme (semantic preferred) and changelog feed will keep everyone on the same page.

I’m open to the toolchain—InstallShield, WiX, NSIS, pkgbuild, DEB/RPM, Squirrel, or whatever you think best—so long as the final deliverables are properly signed and professional on every platform. All scripts should live in source control, and I’ll need clear documentation on how to reproduce a build or cut a hot-fix.

Deliverables
• Signed installers for Windows (EXE/MSI), macOS (DMG/PKG), and Linux (DEB/RPM)
• Licensing system that emails keys immediately after purchase or code redemption
• Built-in telemetry feeding a private outage/usage dashboard
• Auto-update service with version checks, background download, and safe rollback
• Reproducible build scripts and concise hand-off documentation

Let me know which tooling you would choose and show me a past project where you solved a similar packaging and licensing challenge.