Have not seen this before in stores that we have migrated so far. But perhaps you could follow the steps Magento 2.3 takes to determine if an order can be reordered or not.
The logged in user needs to have permission to use the reorder function. (I assume this is the case since you can reorder other orders). - Magento\Sales\Block\Adminhtml\Order\View::...
You can fix this issue by adding temporary solution adding simple condition in Magento\ConfigurableProduct\Helper\Product\Options\Loader::load(ProductInterface $product) after line no : 51
if (get_class($typeInstance) == 'Magento\Catalog\Model\Product\Type\Simple' || get_class($typeInstance) == 'Magento\Bundle\Model\Product\Type')
For the get Customer Order history use searchCriteria and passed customer_email id.
Follow below Magento 2 API to get the customer order history.