Eves: If you use a credit card, you have to put your billing address. If you live in NY, iTunes (or other such services) will add the tax.
Seems like gift cards might be a way of by-passing that. Do they take pay pal? Just seems like there would be ways to avoid the tax if one chose to. Plus there is that whole thing about how online merchants are generally not too keen on the notion of paying to states. Thats why sales tax is only applied to online purchases when the store has a physical presence in the state.