My working assumption is iOS 13 will drop support for the 6/plus alongside the 5s. They even called out the 6 plus as a device that benefits from iOS 12’s optimisations. I would be very surprised if the 6s was also dropped though. Apart from that being a lot of hardware to cut out at once, the A9 is a lot closer than people realise to the A10 - while the A10
has four cores, it’s not a quad core processor in the traditional sense as it can only ever use two at a time. The more powerful pair of cores are a relatively small bump over the A9. I would say A9 becomes the cutoff, with the iPads Air 2 and mini 4 (A8 and A8X but with 2GB RAM) possibly also getting an extra years’ reprieve.
The dark mode and redesign will most probably happen. We have seen dark mode on MacOS so it’s a safe bet the iOS version won’t be too far behind. As for the redesign, it’s meant to be a mainly iPad thing, and with the new iPad Pro hardware I think they will be eager to really do something to do the hardware justice.
Higher iPhone ‘XI’ prices will probably be dictated more by if they include more expensive hardware like under screen Touch ID (in addition to Face ID) which will also have a R&D cost associated with it. From what Tim Cook said about pricing, I would imagine they might try to build the XI series devices to an $899/$999 price point this year, and maybe even lower ($699) for the XR successor (possibly meaning back to 32GB entry storage
)