The IRS can waive the 60 day window in some instances such as when the delay was beyond your control (think disaster or if the bank or trustee fouls up the transfer).
To be sure, Obama has been battered by a series of struggles, starting with the economy, but including a series of events that were at least initially beyond his control -- from the Gulf oil disaster to a Republican minority that by any objective standard has tried to block him at every single turn -- and dragged down his approval ratings.