I would like it so only new players to the server get the init popup info window.  After that they would no longer get the popup and type /info instead.  Is there any possible way to make Server info only show for the very first time a player joins the server?  Maybe via a permission group?

no it is not programmed that way.

Yes but it could be possible?  Like the Noob Messages plugin.  After a new player joins, a permission is added so they don't get the message again.  It would be nice if the plugin supported that.