We have several closely related issues that I'm closing to be addressed altogether on this issue instead:
https://github.com/Automattic/woocommerce-services/issues/1819
https://github.com/Automattic/woocommerce-services/issues/1903
https://github.com/Automattic/woocommerce-services/issues/1885
https://github.com/Automattic/woocommerce-services/issues/1818
https://github.com/Automattic/woocommerce-services/issues/1865
@elizaan36 is working at looking at the overall design here
This Spike was done to determine how we should store/transmit the needed data to address all the above issues.
https://github.com/Automattic/woocommerce-connect-server/issues/1347 is for the Connect Server implementation of this work. If this issue is worked on at the same time, we'll need to coordinate on what the API interface will be.
@c-shultz @aleftick
Here's a solution for better displaying the service options, shown for desktop and mobile. Probably not final but I'll post them here so we can discuss.

Quick walkthroughs:
Desktop
https://share.getcloudapp.com/kpuY98GE
Mobile
https://share.getcloudapp.com/eDuxWXmG
Also included a solution for better displaying the WCS savings. This would appear as a notice below the totals.
Here's the Figma file for these designs: https://www.figma.com/file/fcebyhNqZ9RhkFUzPHAtUG/WCS?node-id=1%3A1832
@c-shultz the only change I made based on the feedback yesterday was to add in "signature required" as a differentiator to choosing USPS Express mail. (edited from _Requirement > required_ cc @aleftick)

Hey @elizaan36 :wave: I have a question about the signature options. Since they're checkboxes, what would happen if the user clicks the two options in the last screenshot?
hey! They can only select one or the other. They appear as checkboxes but they behave as radio buttons. I know it's not ideal, but we need to allow users to De-select the checkbox as well, which doesn't make sense with radio buttons.
Let me know if you want to jump on a slack call anytime to walk through the prototype.
Thanks @elizaan36! Ok, I'll do that. The rest of the prototype is crystal clear, I just had doubts with that part. But I'll ping you if I need any clarifications. Thanks again!
Most helpful comment
@c-shultz @aleftick
Here's a solution for better displaying the service options, shown for desktop and mobile. Probably not final but I'll post them here so we can discuss.
Quick walkthroughs:
Desktop
https://share.getcloudapp.com/kpuY98GE
Mobile
https://share.getcloudapp.com/eDuxWXmG
Also included a solution for better displaying the WCS savings. This would appear as a notice below the totals.