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Not sure about skipping the picures.
IMO the easier way to do it is to take one of the pictures and then take the opposite path after beating It Lives (either polaroid + Sheol or the Negative + Cathedral). That way you'll still get the picture's passive benefits (invincibility on hit or necronimicon effect) without having to do an extra floor.
I'm not sure if Greed Mode counts for win streaks or not. I heard from somewhere that it can count but your final run has to be in the regular mode, but take that with a grain of salt because as far as I know that's unverified.
Another thing to keep in mind is that you can't reset a run once you've gotten your first win, since resetting (even if you don't die) will reset your win streak.
So taking Polardid and going to Sheol and taking Negative and going to Cathedral and Greed Mode will not end your strike and you still get 5 Nights at Mom's. Not sure about 3th and 5th run needed to be not Greed Mode run because I didn't test it.