Decided to test my suggestions. This setup took about a half hour to set up and animate:
This is essentially what I described but in actually walking through the steps, I found ways to simplify it a bit.
In the above, I'm using two Switch layers, and when the flying card snaps back to the start position, both Switches advance to the next card in the sequence. Using Timeline Visibility, it's easy to make sure the switches and bones animations stay in sync.
I'm using dynamic parenting to parent and release the first Switch group's bone from the left hand bone. The card bone is re-parented after the card goes off-camera. The second Switch group's bone is parented to the right hand bone and is released at the end of the animation.
As mentioned earlier, this works if the card goes off-camera, however, if you reveal static versions of the cards on the ground when the flying card rests, you can do this with a wider full-body framing.
If I was doing this for real, I'd also use animated layer order to move the card from behind the right hand to in front of the right hand as the card is being tossed. In wider angles, I'd probably add some 3D rotations to the cards.
Here's the project file. Hope it helps.
DylanTest