The Future Simon we see in season 2 is a version from a timeline where the ASBO 5 went public, without being rewound by Curtis. We know this because he had the footage, which he could not have had from Curtis' memory alone.
With every loop, an additional parallel timeline comes into existence, which is not exactly identical to the last ones, even though the causality "Future Simon seduces Past Alisha -> Past Alisha inspires Past Simon to become Super Hoodie" happens in most of them. There must have been a first one where Future Simon never arrived and a last one where Past Simon never travels back.
Season 4 takes place in the timeline we saw develop in season 2 and 3, with all Simons and Alishas now being dead. But the time travel power Simon uses at the end of Season 3 starts a new, parallel timeline where he can save Alisha AND warn her so that her throat doesn't get slit.
Future Simon has the time to make new suits, he doesn't necessarily use the one he inherited from another Future Simon. Maybe this explains why the masked guy at the end of season 1 looked slightly differently (I thinknot the same mask).
The Jewish guy who travels back in time uses a different power than Curtis. Seth indicates it's the same, but it works differently than sending just memory, so maybe Seth got confused with at least three different time travel powers out there.
And we have to assume Alisha probably tells Simon about his future self even after Curtis rewinds the ASBO 5 going public sideline within the timeline we see in season 3. She can't keep this from him forever, and doesn't really want to.