Is it possible to add buttons from two different addins (one office web addin, and the other VSTO addin) in the same custom ribbon tab in office 2016?
If yes, how?
I don't think so, but this should be something you can determine by a quick test. Define a tab/button in VSTO and then define an Add-in Command for the web add-in and use the exact the same name for the tab in the manifest of the web add-in. I suspect you'll get a two tabs with the same name.