>>when is it time to let them be in the same room like our family room to run around without one of us holding the new kitten? and what should we expect?

If the older cat is still hissing, I'd wait another week before letting go of the kitten entirely. Try the carrier a bit more. Also see if you can feed them far apart in the same room with the kitten in fast grabbing distance. If this works try letting the kitten go and see if you can get them both playing with some sort of cat wand.
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Smile, it will make them wonder what you are up to!

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