Hello Shuesawhau82
Even a three-minute change at Lugano station is possible. We Swiss do like it efficient, long transfers and waiting at the station is not what we like. Therefore, the timetable would not suggest an itinerary that is not doable. 14 minutes is three times what you will need to change platforms.
I think you mean your Swiss Travel Pass (SwissPass is a resident offer). Your Swiss Travel Pass covers your travel to Chiasso, the border station, albeit you are changing trains already at Lugano. Thus, you simply need a ticket from Chiasso to Milan. Tickets for the RE trains are solely valid on RE trains, not on EC trains.
Kind regards,
Roland