Allowing additional evaluation time to users after switching to paid

I recently changed my app from free to paid via Atlassian model.

A customer is getting a notification that they would be updating to a paid version, as expected:

My question is what they should expect after clicking the “Paid Update” button:

  1. Will they be able to start the 30 days evaluation even though they already tried the free version?
  2. Will they be able to see the pricing before approving the upgrade and getting charged?
  3. If they uninstall the app and install again - will they be able to enter the 30 days free evaluation again?
  4. Do I, as a developer, have a way to simulate and test out this flow to learn better about the experience of my customers?

Thank you for your help!

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