I'm currently able to change the way the cart works by updating the qty value in the cart, i do this by first deleting the item before it is re-added using the checkout_cart_product_add_before observer.

Here is my observer class (the simple products work but the configurable products do not delete)

namespace XX\XX\Observer;
use Magento\Framework\Event\Observer;
use Magento\Framework\Event\ObserverInterface;
use \Magento\Checkout\Model\Session as CheckoutSession;
use \Magento\Checkout\Model\Cart;
use Magento\ConfigurableProduct\Model\Product\Type\Configurable;

class DeleteAndReAddFromCart implements ObserverInterface {
    protected $request;
    protected $_cart;
    /** @var CheckoutSession */
    protected $checkoutSession;
    protected $configurableproduct;
    public function __construct(\Magento\Framework\App\RequestInterface $request, cart $cart, CheckoutSession $checkoutSession, Configurable $configurableproduct) {
        $this->_cart = $cart;
        $this->request = $request;
        $this->checkoutSession = $checkoutSession;
        $this->configurableproduct = $configurableproduct;
    public function execute(\Magento\Framework\Event\Observer $observer) {
        $info = $observer->getInfo();
        $order = $observer->getEvent()->getOrder();
        $product = $observer->getProduct();
        $productId = $observer->getProduct()->getId();
        $prodtype = $observer->getProduct()->getTypeId(); //is configarable or simple
        $info = $observer->getInfo();
        $items = $this->_cart->getItems();
        $itemCount = count($items);
        if ($itemCount > 0) {
            if ($prodtype != 'configurable') {
                foreach ($items as $item) {
                    if ($prodtype != 'configurable') {
                        if ($item->getProduct()->getId() == $productId) {
                            $itemId = $item->getItemId();
                    } else {
            } else {
                $product2 = $observer->getProduct();
                if ($product2->getTypeId() == "configurable") {
                    $configClass = $product2->getTypeInstance();
                    $childProduct = $configClass->getProductByAttributes($info['super_attribute'], $product2);
                    $productIdd = $childProduct->getId();
                    //the above id is the correct id of the simple product
                    $c = $this->_cart;

its the code below this condition

if ($product2->getTypeId() == "configurable") {

condition thats not working, the simple products above it successfully remove from cart.

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