When attempting to change the "requested target" I am receiving an error related to a field that was previously filled in.
Error
There are fields that are required or in an error state, but the administrator has hidden them or made them readonly using a behaviour.
customfield_12703: Issue: PM-5317 does not fit filter query: project = "PM" AND issueType = Initiative
This is broadly what it says it is - there is a Behaviour in play that is stopping you from entering data into a required field that is currently empty.
You'll need to fix the Behaviour so that it lets you get to the required field, or get something into the field another way before changing the type.
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