Hmm... Canon points are proving Fun to finagle between AoS and the rest of the MCU. Early seasons have a few major benchmarks and then they just kind of... went off and did their own thing, so I've taken to sort of smooshing/condensing the AoS timeline as needed to make it fit and still have good character development. Because really, what is time in this universe, anyway?

Tl;dr: I can work well with anything post-Ultron and the big SHIELD is Hydra reveal, depending on when you'd want to take Tony from and whether you want the huge angst-fest of post-Civil War or post-Snap.