1

As a practical matter—is it better/easier/more advisable to upgrade to Calendar 2 before upgrading to ExpressionEngine 3, or the reverse?

2

You cannot upgrade to Calendar 2 while on EE2, as it is only compatible with EE3. We created a very thorough walkthrough and user guide for customers wishing to upgrade from Calendar 1 / EE2 to Calendar 2 / EE3 here:

https://solspace.com/expressionengine/calendar/docs/calendar-1-migration/

So to exactly answer your question, you need to upgrade Calendar and EE at the same time (take site offline, upload EE3 files, upload Calendar 2 files to EE3 addons folder, then upgrade EE. Then upgrade Calendar, and update your templates). :)

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