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• 1) Implementing this really wouldn't be all that hard because you would use existing components like perl, spamassassin, ssh, and rsync.
• 2) You would need to tie them all together using some toolkit to make a frontend like gtk or qt that works in Cygwin. From the frontend you choose mail client folders to read for HAM and SPAM, and schedule the nightly mass check time.
• 3) You might need some kind of service or applet visible from the systray in order to do the scheduled nightly mass check.
• Wiki Markup4) Use an "InstallShield" type click-thru installer, which seems to be the standard on Windows. They shouldn't need to make \ *ANY\* choices to download and configure Cygwin. It should just dump everything needed into a single folder that contains this mass check bundle. (use \[http://nsis.sourceforge.net NSIS\] ?)
• 5) The use of existing FOSS components and a cross-platform toolkit like gtk or qt would allow this to build on Linux too.