Unfortunately no carrier including Rogers does this. You can upgrade to a new device BUT you will have to pay the flextab owing from the previous device u got with Rogers. No carrier does trade ins like this sadly.
You can also sell your device on a website or to a family friend and put that money towards the new one.
So in order to get a new device with Rogers , you will have to pay the owing flextab balance and also the device price of the iPhone 5 on a 2yr term unless it shows $0. Also to remind u that u also need to pay the $20 connection fee.
My daugher switched mid contract, so I bought out her current phone at what I considered market value - she was happy with it - I bought it at 75% of her pay out price.
So yes, look to see if people want to buy your phone. You can get the Moto G4 plus on amazon for under 400.00 unlocked, so pay 50.00 to unlock and sell, or sell it to them a bit lower and they can unlock or not. Be careful about unlocking and making sure that you get it done in the right order so it does not get black listed in error.
Always someone who wants to buy a phone at a discount and you can recover most of your tab. We have done that a few times with broken phones, not wanting to use the poor replacement phone during warrenty repair. Buy a rogers locked replacement of Kijiji, then when it was time to get the new phone, cell it back through kijiji. Someone is out there who wants a Rogers branded phone to replace their damaged phone, or just get a deal on last years model.