I'm pretty sure the reason the flight status is always out of whack is because this guy is making all the changes to the database manually.

Honestly, I suspect their flight management system maps flight statuses poorly to the web information. At minimum, I bet "pushed back," "taxiing," and "sitting on the tarmac for no apparent reason" all show up as "In flight" on the website. The only status messages I've seen on .bomb are "Not Departed," "Canceled," "In Flight" and "Arrived." Are there others?

In reality, there are, of course, hundreds of other possible statuses including "boarding," "deplaning," "queued for takeoff," and "crashed." But they choose to simplify things.