So it ended up being a stuck cron job that clears pending payment status’ after a certain amount of time. Once I got the cron unstuck it started working as expected. I am seeing some errors showing in the admin with the newest version of the plugins though.
Notice: Trying to get property ‘total’ of non-object in wp-content/plugins/sezzle-woocommerce-payment/woocommerce-gateway-sezzle.php on line 641
Looks like you are hooking into the woocommerce_available_payment_gateways filter and checking for a total in a cart object. Can fix this on line 640 with a if(is_admin()) return $available_gateways;