I think November 2019, at that point the PS4 will be six years old, PS4 Pro will be three years and they will be able to have another reasonable upgrade over the Pro and a big improvement over the base PS4. I expect them to keep the mid gen console plan and release a PS5 Pro in 2022.
The PS4 will still be selling but it will have passed it's peak year and be in decline. I don't think Sony will want to hang on to the PS4 for too long as their primary console, though it will be supported for some time to come as is usual for Playstation consoles. I don't expect PS4 Pro to be used as an entry level PS5 with forwards compatibility, since Sony have said they plan to have clean breaks between generations, or for there to be two PS5 SKUs (a base and pro model) at launch.
It's possible that they could delay until November 2020 if PS4 is still too strong to replace but I can't imagine they'd wait any longer. I don't think it's unreasonable to think Microsoft are targeting 2019 as well for their next console, the Xbox One X will probably just serve as an entry level Xbox Two (they have stated they prefer the idea of iterative console releases with forwards and backwards compatibility) and they probably don't want Sony to steal all the hype of having the only "next gen console" for a year or more.
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