Setting Sales Tax for Canada & New York

I've looked for the answer to this but haven't had any luck.

We have a shop located in Portland, Or. We were shipping to US and CANADA and only charging sales tax to customers in CANADA. This worked well.

This past fall we opened another shop in NEW YORK. By having a physical location in the state of NEW YORK, we are required to charge state sales tax for customers in that state even though we are shipping from OREGON. By doing this, I don't have a way to charge CANADA tax anymore.

I need a way to do the following:

1. NO SALES TAX FOR 47 STATES
2. CHARGE SALES TAX FOR NEW YORK CUSTOMERS(SELECT PRODUCTS)
3. CHARGE SALES TAX FOR CANADA CUSTOMERS(ALL PRODUCTS)

If there is no way to do it natively, that's fine. But, is there an addon that can make this happen?

Silly question - I understand the NY tax, but why Canada?

I know, it does sound silly. The main reason is that the customers who purchase our products who live in Canada are required to pay taxes on their purchase regardless of origin. Our customers have requested to pay the duties and taxes while purchasing the items to avoid extra duties and taxes imposed by UPS when importing the product into Canada. So, we facilitate the tax payment process for our customers.