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For me it's PS6 in 2026. Makes the most sense overall as far as I'm concerned, for Sony anyway.

PS5 Pro in 2024, to me, seems like Sony would be putting a target and some heat on Series S. MS would have to answer within a year with a new console, and based on their direction, there won't be any new next gen marketing. It'll just be a new XB, maybe called Series something, maybe not. Point is once a PS5 Pro launches, devs who aren't exactly thrilled about Series S, will be extremely unhappy about it, and even more so with a new top XB.
MS would likely be pressured into discontinuing it if they didn't plan on it. That wouldn't be terrible for MS though because that would give Series S 4-5 years on the market which is enough.
Whether MS would require devs to keep making Series S games would be the next question. After 5 years I could potentially see MS dropping Series S support, but before that would be questionable. If MS did keep supporting Series S after a new top tier model was introduced, they would have to allow devs to drop the quality of Series S games substantially. I don't see this being a huge problem for MS though, as plenty of gamers will be fine with 720p/30 low quality on their outdated Series S. Those who aren't will just have to upgrade to Series X, and the way MS has been handling hardware, it wouldn't be a surprise if they had a decent trade in plan for those gamers.

How many would upgrade from Series S right away? How many would get a Series X if it's all that's available, or the new XB if it's ready by late 2024? How many would switch to the PS5 or Pro, especially if Pro was out 1 year before the next XB upgrade?

To me, waiting until PS6 is best choice for Sony right now, but also would be best for XB and MS. Maybe Sony thinks PS5 Pro would be a little worse for them, but would be far worse for MS?