If it installs but is inactive, it probably throws an exception at startup.
I would wrap all your startup code (ThisAddIn_Startup inside your ThisAddIn.cs) inside try {} catch {} and log all errors on disk so that you can understand why Outlook disables your addin.
You tried to set the environment variable VSTO_SUPPRESSDISPLAYALERTS to find out if you can get a forecast to give you more information?
(By the way, I discovered outlook VSTO to be flaky. Sometimes they just refuse to install and work.)
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