Regardless of what you do there is always a hierarchy and the old dog will be above the pup in that regardless of anything you do. Nothing you do negates a hierarchy and you only have to maintain what you always have to be seen at the top of the ladder. I definitely think a pup should come in before the old dog goes, some good common sense offered here and so long as you are happy that the old dog won't have too many habits you don;t want passed on you should be fine.
On the jealousy count, you control that. If the older dog shows any aggression or jealousy is when you step in and let the old dog know you won;t tolerate bullying or aggression to the other dog. It won;t require physical punishment, just admonishment, if the old respects your position it will get the message. Jim is right, kennel them and train them separately.
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