Hi @nikzaff, welcome to the Sonos Community, and thanks for the interest in upgrading to our newer products. About the Trade-Up Program, you can choose any Sonos product of your choice to replace your old ones. If you prefer to get the same functionality as your Sonos Connect, yes you’d need to get a Sonos Port. Based on customer feedback, we’ve added new functionality that creates versatility with Port. This includes an updated digital-to-analog converter for even clearer sound, a 12V trigger to automatically turn on most amplifiers, and support for Apple AirPlay 2. Also, we’ve recently improved audio quality on Port's Digital Output. We can also wait for other’s feedback and suggestions. Hope this helps. We and the community are always here to help.