Hi Jesse. Thanks for this input. While text boxes cannot yet be tied to date ranges in Organizer, our team has been thinking about ways to improve the process of entering and discovering comments around data.
What some of our customers do in this scenario is have an Organizer Topic for each week, and they can navigate to a Topic representing a week in the past when they want to see what comments they had entered alongside the data. Some users duplicate that report each new week and clear out comments that may not be applicable when entering in new comments, and step the date ranges to now. This would be my recommendation for the time being.
Another route you could explore is Annotations in Workbench. They have a date/time context and can appear on the trend as a little chat bubble, but the information added there is not yet available in Organizer. We hope to bring the concepts of Annotations in Workbench and Comments entered in Organizer together some time in the future. We might reach out for more feedback from you on these ideas.