I'm not seeking to defend Mr Crewdson's oeuvre, but it seems to me to be an extreme example of the practice of constructing the subject of the photograph in ideal conditions approach as opposed to observe the subject and make the best of the conditions in which it is found. Sometimes when Sydney throws up an extended period of lousy light I have a crack at still life and take some care with subject arrangements--wouldn't you?
Mr Crewdson's images may be ultimately banal, but they are easier to grasp--conceptually--than Damien Hirst's assistants' work with skulls, sharks and cows.
If nothing else a purchaser of a Crewdson print may be able to see why the damn thing cost so much; there's a TV series running on SBS about big moves, usually of buildings, which offers insight into the cost of closing down a street and urban facilities to do this sort of exercise, maybe they could do a series called "Monster Pictures"
(what's a "chooch"? I could use that word)
Regards - Ross