I love this community.
Just to check I understand you Wraithlord: The way you've described your script, it sounds like it essentially performs the same tasks as the LlamaServer, i.e. kind of the opposite of what we want to make. So is the idea that your tool contains all the essential elements (especially e-mail checking and sending) that could be cannibalised into a new tool?
Also, one difficulty I was anticipating with Windows is that it doesn't have a perl interpreter by default (and all my LlamaServer code is in perl). Would the same issue apply to Python?
Oh, another thing - am I right in understanding that CLI means it's a command line program? Is there any way to make it easy for Windows users to use without opening a DOS window? i.e. could they just double click on it?