Explanation

* Retention wins over deletion. Suppose that one retention policy says to delete Exchange email after three years, but another retention policy says to retain Exchange email for five years and then delete it.
Any content that reaches three years old will be deleted and hidden from the users' view, but still retained in the Recoverable Items folder until the content reaches five years old, when it is permanently deleted.
* The longest retention period wins. If content is subject to multiple policies that retain content, it will be retained until the end of the longest retention period.
Box 1: No.
The file will be deleted and hidden from the users' view, but still retained in the Recoverable Items folder. An administrator would need to recover the file.
Box 2: Yes.
The file will be deleted and hidden from the users' view, but still retained in the Recoverable Items folder. An administrator will be able to recover the file.
Box 3: Yes.
2018 to 2023 is five years. Policy2 has a retention period of four years. However, Policy2 is configured to not delete the files after the four-year retention period.
Reference:
https://docs.microsoft.com/en-us/office365/securitycompliance/retention-policies#the-principles-of-retention-or-