Custom Order Status + WC Hooks

Curious can I do the following with your plugins?

Q&A #1: Additionally, with the PRO version. Can I do the following use case scenario:
Send 1 email to 1 particular customer (e.g. Vik Smith) using an email template AND … I want to attach certain image/s that are specific for this customer?

Q&A #2: IN our case, we sell custom saunas. We want the customer to approve their sauna layout diagram. IDEALLY, it’d be amazing IF they could click a button in the email itself which would change their ORDER STATUS = “Diagram Approved” Or prompt them to login and change their Woocommerce order status