Ah, I've found a season 4 timeline that actually makes some sense and tries to give specific months and years when possible. At the end, it points out the big continuity problems like the drone strikes, Tobias's "three weeks" of wandering around, and Pete dying in 2011 but his death being referred to years earlier, before Lucille's trial.
I am surprised that they have Lucille's trial occurring in May 2007, though. I thought it must be in 2008, given that Lucille Austero's checkbook had an entry for hundreds of dollars worth of juice boxes on May 1, 2008 (the day she wrote a $700,000 check to Michael). The Wikia timeline also ignores the problems at the family meeting/graduation party, where Buster says that Christmas was "seven weeks ago." May is not seven weeks after Christmas; it's more like 20.
I disagree that Maeby was living in the penthouse for very long. It looked more like she spent one day there, then was forced to leave for the model home. The narrator even clearly says that Maeby doesn't decide to go back to school yet again until she discovers that she can't get internet in Sudden Valley. That's when she starts having her 3rd, 4th, 5th senior years. Also, Lindsay moved into the penthouse because she just heard from Marky's mother that Lucille was in prison. Why would Marky's mother learn this news 4 years after the trial? Joan Bark also keeps calling Lindsay "new girl" and confusing her with DeBrie, while Lindsay says that she cut her hair, implying it was recent. Also Marky says that the ostrich farm is being driven off the land. Who's driving them off? The neighbors at the sweat lodge retreat? The new owner of the land (i.e. George Bluth)? Why would Marky delay doing the scary Ostrich Vision warning for four years while the neighbors were numbing the local wildlife? This move can't be delayed until 2011. It just freaking can't.
Therefore it must be within days after Lucille's trial when Lindsay took Marky and the ostrich to live at the penthouse. The flaw is that the timeline is trying to place these events in 2011, the year before the election stuff. It's the damn narrator saying that only "one year" passes from the Ostrich Vision to the Herbert Love rally that screws everything up. If he'd just say "four years" we could skip cleanly from 2008 to 2012.