Troubleshoot Magento - 2 Bugs

We have a live Magento site that needs two issues troubleshooted and repaired. 1. Troubleshoot and repair: The automated email that goes out when an order is shipped is not sending to the customer. The admin does get a copy of the email, but the customer does not. (Need this working for both credit card and paypal customers. 2. Troubleshoot and repair: This site uses WebshopApps MatrixRate for shipping calculations. Orders from Canada are not being charged any shipping and should be. For our site, the MatrixRate data-table is configured to use flat rates based on Country/Region/State/ZipCode only (no weight calculations) with no International rates shown other than Canada. The Canadian and USA rates are already in the uploaded table - but something isn't working correctly since orders from Canada are not being charged anything. Important Notes: 1. This Magento site is on a Windows server - not linux. 2. Due to the smaller size and scope of this project, 100% of payment will be escrowed and made upon satisfactory completion of the work. Please see our feedback regarding our excellent payment history. We are looking for expedited repair of this issue.