Using cygport, I think that packaging has become quite easy now. At least, once the cygport script is built and working, updating a package to a new release is as easy as updating the version number in the cygport script, then running 'cygport ... download all'.
Except for one thing: the upload step. Maintainers still have to go through the procedure at https://sourceware.org/cygwin-apps/package-upload.html. Although it's easier than the old manual upload process, it's still a little tedious and error-prone. Yaakov, would you consider adding an 'upload' command to cygport, that would handle the uploading details? That would take away the last bit of manual work in a routine package update. If you don't have the time or interest to add an upload command yourself, would you consider a patch? I've spent some time looking through cygport code, and I might have time to give it a try, or maybe someone else would. Andrew