To answer your question, it's not possible to programatically re-enable your add-in from the add-in itself. Think about it - it doesn't get loaded, so its code won't get run. So nothing you put in your code will re-enable the addin, because it won't get executed.
The only way would be to create a watchdog process that checks if the COM add-in has been disabled every 10 minutes or so, and re-enables it. You'll need to know where Word stores those settings though.