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The best time to flat iron is best shortly after a blow out. That way any sebum oils wont ruin your out come. also its better to flat iron on cooler, low humidity days to prevent the chance of your hair poofing up.
I always air dry/wet wrap and then flat iron the next day. I never blow dry my hair to flat iron (yet, I anticipate having to do this when it gets longer) but with my NL hair I can get away with air drying/wet wrapping and then flat ironing. Thats how I used to do it anyway.
Now I just wrap it nightly when its straight and by day two its as flat as it would be if i flat ironed it.