I don't know about the expert status, but I'll try to help where I can.
Actually, chocolatey discourages the creation of a separate dev-stream for a software. It has the --pre switch to install pre-release versions. That should work as long as the choco packages have according versions for the dev builds. Looking at this issue I don't think choco supports Semantic Versioning 2.0.0 just yet (e.g. where you could do 5.0.0-alpha.1), but 5.0.0-alpha-20190930 would also work. Precedence is determined by lexicographic ASCII sort order. It's encouraged that the package version follows the software version.

I haven't had your case yet, because I'm not the vendor of any of the software I maintain in the chocolatey community repository. I found it easiest to use the AU Powershell module for my situation.
The packaging requires basically only 2 files: the nuspec and the tools\chocolateyInstall.ps1.
You can either replace certain strings using regex or write the file fom scratch. In the nuspec you would replace the version and the release notes, in the install script the URLs and checksums (and fileType if you have an MSI instead of an EXE).
The AU module makes this easy as you can see below in an example.

function global:au_SearchReplace {
    @{
        "tools\chocolateyInstall.ps1" = @{
            "(?i)(^\s*packageName\s*=\s*)('.*')" = "`$1'$($Latest.PackageName)'"
            "(?i)(^\s*fileType\s*=\s*)('.*')" = "`$1'$($Latest.FileType)'"
            "(?i)(^\s*url\s*=\s*)('.*')"        = "`$1'$($Latest.URL32)'"
            "(?i)(^\s*url64bit\s*=\s*)('.*')"   = "`$1'$($Latest.URL64)'"
            "(?i)(^\s*checksum\s*=\s*)('.*')"   = "`$1'$($Latest.Checksum32)'"
            "(?i)(^\s*checksum64\s*=\s*)('.*')" = "`$1'$($Latest.Checksum64)'"
        }

        "$($Latest.PackageName).nuspec" = @{
            "(\<releaseNotes\>).*?(\</releaseNotes\>)" = "`${1}$($Latest.ReleaseNotes)`$2"
        }
    }
}

I have it all run online online on appveyor on a CRON job. But for simple string replacement you wouldn't need any of that, I guess.

If you have your nuspec and chocolateyInstall.ps1 files ready, the only thing left to do is choco pack and choco push. You would need your choco API key and the status of a maintainer of the package in order to successfully push.
So, the aforementioned chocolatey GH-action actually sounds like the way to go.

When the names/URLs of the install files don't change and aren't avaible anymore with each new build, all the pre-release packages will be broken on a daily basis if they just link to the same URL and the hashes don't match. Alternatively, you could package the MSI or Zip with the choco package. Then all older versions would be still available on choco.

PS: I didn't even know about the portable version. We should add that. There would then be a virtual package jabref, that really doesn't do much except having a jabref.install package as a dependency, and a separate jabref.portable package.

Uh oh!

Make development version/snapshots available in choco community repository #5031

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