In a nutshell:
Sent $2500 to a person based in Japan for Japanese goods.
$1500 of that came directly out of my bank funds.
He issued a refund to me a few hours later because I sent it to his American-based PayPal account and it needed to be sent to his Japanese-based one instead (as his Japanese-based PayPal account is tied to his Japanese bank account, where he lives, so can add the funds to his bank there).
Upon seeing he refunded me in PayPal, I immediately re-sent the amount to his Japanese-based PayPal account.
However, it apparently takes 3-5 days for PayPal to refund the $1500 I took from my bank funds back into my bank account. I don't know why they didn't mention this in detail somewhere on the refund details page; you instead get a vague "It's on a temporary hold, we'll contact you soon," response.
As I didn't know this, and upon immediately re-sending the payment, PayPal charged me $1500 again on my bank account. This is because the original refund did not yet go back into my bank account.
My bank charged me an overdraft fee because of this. Great.
Shortly after, PayPal sent me an e-mail saying there's not enough funds in my bank account (obviously) for the $1500 they're trying to take out again.
So my question is: Whenever PayPal finally puts the original refund of $1500 back into my bank account, will they automatically take it back out to cover the re-sent payment I sent? What happens if PayPal decides to take their time with refunding my bank funds back into my bank account and see they still don't have that money back for the re-sent payment I sent? What would happen?
I've called a couple times asking these questions to PayPal, but am pretty certain their customer service is outsourced to another country as it proved difficult not only to get my questions across, but also to get a sound answer. I could tell that they just wanted to get me off the phone as quick as possible so I can't take the credibility of their answers too serious.
