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The movie wasn't as complicated as you're trying to make it. The son was never in two places at once. They just did not show the film in chronological order as they lead you to believe.
The people were put in the house up to three days before the cops raided jigsaw's building. I'm guessing they were in the house before the deathmask murder of the detective's informant because Jigsaw and Druggie wouldn't risk them noticing the steel company's logo and raiding the place before they were ready.
Also, It wasn't guaranteed that the druggie and the son would survive. Not even jigsaw could know who the crazy guy would throw in that pit of needles. There were some very "scripted" things that the druggie did to encourage different emotions and get escape from crazy dude. They probably had all their bases covered, if the son and druggie had died jigsaw would have had time to compensate and come up with a different game to play with the Detective.
I can't explain it any better :/
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“It is better to be rich and healthy than poor and sick” - Dave Barry
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