While I never had any luck getting help from Squarespace or PayPal, I figured out a solution! The PayPal account that you're syncing to needs to be linked to a credit card or debit card and if there isn't one linked, it likely won't prompt you to fill in that information. When I went in and manually set up the card in PayPal and then went back to reconnect, it finally worked! I'm surprised how difficult it was to figure out this simple step, but I've been able to successfully sync 3 clients to their PayPal with this method. Hope this helps!