Entering USA under VWP while also being a student
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It seems to me like you're making this too complicated for a vacation. If the border officer asks why you're switching passports and statuses, how will you explain it? This kind of tricky solution might sometimes be expedient for someone who suddenly needs to travel for an unforeseen emergency (like a dying relative, etc.) if they can't get their usual passport or visa in time, but it doesn't seem appropriate for your case.
The simplest solution is to get your new DS-2019 soon (preferably before you leave the US), renew your A passport soon (also possibly before you leave the US), renew your J-1 visa abroad, and then return to the US with valid J-1 visa and DS-2019. This should be the simplest solution even if all you're doing is tourist activities for two weeks. If you're having trouble getting your updated DS-2019 soon enough, you should first talk with your school's international student office and explain your situation. They should prefer to help you get the right documents earlier, in order to help you avoid the situation of needing to switch passports and statuses.
Note: I'm assuming you need a new DS-2019 only to extend the end date, and that it will already have a travel signature when you receive it. If you're actually changing to a different J-1 program with a different SEVIS ID, the advice would be different.
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