Anyone tried to use the same paypal account for two different Humble Bundle accounts?

My imagination.
I paid for HumbleChoice.
I paid HumbleChoice as a gift for my friends.
Do you have two bills?

In any case, it's safe to ask Humble support.

I did. A few years ago it worked without problems. I stopped buying bundles for a few years and when I got back to it about half a year ago I wanted to buy a bundle I already bought for myself for my son as well with my second Humble account/same PayPal. I got an automatic message that my order was cancelled due to limited supply and that they didn't charge me any money. So I sent a mail to support and asked why I couldn't buy another bundle for my son. They manually checked my accounts and realized I wasn't a greedy reseller, so they allowed me to buy another bundle.

It's possible to buy two bundles with the same PayPal, but if you do it too often and/or give away your keys/gift links to a bunch of people all over the world they will not allow it.