WooCommerce Cart: Add Product after Reaching $ Value

Our Members receive a 25% Discount on their purchases, so at a certain $ value, it becomes beneficial for the Membership purchase "product" (This is not a WooCommerce Membership, rather an external Membership processed separately) be added to the customer's cart, which then applies the discounted pricing (this reduction already works if someone manually adds the Membership product to their cart). However there are some further conditions: 1) Some products already come with a Free Membership and are over that value, so should not trigger the addition of the Membership; 2) Some products are not eligible to have a Free Membership, despite being above that value, so should not trigger the addition of the Membership; 3) Some customers may not be eligible for a Membership so we would like a way (popup or similar) for them to opt-in to the addition of the Membership or at least something explaining what has happened; and finally 4) Some customers may simply change their mind after adding the membership and may want to remove the Membership and we don't want the customer stuck in a recurring loop whereby the cart's logic gets triggered upon refresh and keeps trying to add it back in.