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Most of the folks I know that have done this commute did so at about 5:30 to 6 A.M. They rarely complained about the drive, and they could make it from west Simi Valley (near Madera and L.A. Ave.) or Moorpark to Sylmar (basically @ Roxford and I-5) in about 20 minutes.
Of the people I know that commute into "The Valley," the ones coming from Simi Valley seem to have about the easiest drive, with Santa Clarita being pretty close. It really depends on the part of the valley you're going to. For Sylmar, I think it would generally be a little easier from Santa Clarita, but not by much.
As far as driving on the 5 and 405 for the commute into Sylmar, it would not be much of a problem if he's commuting during normal hours. Once you leave the 118, you are pretty much going against the main flow of traffic, so the 405 and 5 should both be pretty smooth sailing.
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