What you are looking for is the same sort of solution that exists for real, networked systems -- basically a network software deployment tool like https://emcosoftware.com/remote-installer,. Source: over 2 years ago

I’ve had to do this before and it some what sucks but if you do have a look at Inno Setup. Source: 6 months ago

Use Inno Setup. It's comparably sized, VSCode uses it and GOG.com uses customized builds of it (it's open-source but written in Delphi), and it has a much more declarative (though still extensible) approach that does do stuff like uninstall tracking by default. Source: about 1 year ago

We eventually settled on a combination of InnoSetup with InnoSetuo Dependency Installer and NetSparkle which offered a much cleaner experience and use of AzureAD Authentication for Azure Storage Blobs (for updates) as well as InTune Deployments with proper version detection. Source: about 1 year ago

You don't typically make these things yourself from scratch, you use a tool that does it for you. E.g. InnoSetup: https://jrsoftware.org/isinfo.php. Source: about 1 year ago

The two most popular such installers are Inno Setup and NSIS. Inno is much easier to use (and will handle most tasks automatically), while NSIS creates somewhat smaller installers (but requires you to basically micromanage everything). Source: about 1 year ago