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I think we should go for flexible always, do these things you mentioned, but have a better error handling if someone has any type of issue migrating to the flexible.
The reasons for migrating to the flexible:
It doesn't remove any feature from the user
It will allow us to only need to maintain one calendar type
It will allow us to implement a partial waiver (as now we are not tied to 2 or entries)
Just to document that we have this issue in place and it needs to be finalized before the next release happens.
If we go for flexible only:
If we keep them:
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