The free shipping above 99 and flat rate below can be achieved with the core shipping options. Having differently priced options for express shipping based on the order total isn’t possible with the core options though.

I’d take a look at Table Rate Shipping or Conditional Shipping and Payments. Either one of these will let you set up conditions where certain shipping options are offered to customers.

https://woocommerce.com/products/conditional-shipping-and-payments/
https://woocommerce.com/products/table-rate-shipping/

Let us know if you have any questions.