When should you upgrade your phone? Black Friday! Verizon would have given me $600 for my iPhone 6 during their Black Friday promotion, even though it's a two year old model. (Thank you, Apple, for making the silly iPhone 7 change of removing the headphone jack, propping up demand for my aged model). I learned this from a rep as I made my new phone purchase a week later (*single tear*). Other FAQs he answered:
Will you have another trade-in promotion?
Check in around "major" holidays, like Valentines Day or Memorial Day.
What if I want to trade in my phone ahead of a two year period?
Not a problem; if you bought your phone as part of your plan, the financing agreement allows for early trade-ins.
With that info in mind, I *may* just upgrade my phone to the next gen next November if it's shiny enough, and the net cost differential is negligible.
I also finally sprung for the largest storage space, to free myself from the endless loop of deleting phone photos and under-used apps. Now I can re-download Pokemon Go and just worry about battery drainage.