I think it's amazing how fast freeway removals move. many of them are so fast that state DOT isn't prepared for it and might even do work to maintain the about to be removed freeway. With CT 34, obviously ConnDOT didn't know that removal was coming, because there's no need for a flyover like the one they built for a surface street.
It's a question of who's calling what shots. Removing the Oak Street Connector was something the city of New Haven came up with and started clamoring for. ConnDOT wasn't planning for it to happen because it wasn't their idea. So ConnDOT only knew about it once they started getting leaned on to make it happen, it was never in any long range plans and therefore was not considered in any projects prior to it.
As for how fast it moves, well, yeah, it's amazing how fast construction moves when environmental groups favor it and no one tries to sue to stop it.