Hello @obeessub, this is an interesting concept. While we don't offer a completely automated version I have a work around you could implement.
Currently Square's Loyalty program is connected by a 12 digit number than the card used for the transaction. You could create a discount that would allow you to reward a percentage off each time someone uses a gift card. That way the customer will still receive their loyalty point
For reloading the gift card for with a bonus amount, (in this case the extra $2 dollars) I would recomend using Square's split tender option. This would allow you to charge the customers card for $10 dollars and then mark the $2 dollars as cash or other tender.
The only issue here is that your reports will be inflated because of the $2 dollars added each time you reload the gift card. This would make reporting and bookkeeping a challenge.
I will pass this feedback along to our product team! 😀
