We are still optimizing our use of Azure Devops, so there may be a better way to do this that we have not discovered yet. I will share what is working for us right now.
In order to create this type of report using Boards|Queries, we configured additional fields for Product Backlog Items, Tasks, Test Cases, etc. This is done in the Organizational Settings, for the Process that you are using, for the Work Item Types that you want to update.
This will provide access to additional fields to be manually edited for tracking. So far we have used the built-in fields such as Start Date, Finish Date, and others.
We prefer to not have manual fields to support reporting, but if the fields are thoughtfully added to forms it is not too difficult for the team to update them.
If we are missing some built-in features that would provide a simpler approach to your question, I am eager to hear them!