Itamar Tzadok

That's probably one of the simpler use cases the Dataform module is designed for (and it's already developed and available to the community via the plugin repo ... @Howard ).

You can set the activity to Separate Participants to make it individual. You can create a structured entry form with various input field types. You can add grading and feedback fields which the instructor can edit and the student view only and place them next to the content fields. You can create designated grading view for the instructor if needed. You can set the activity grade with a formula to apply different weights to the elements in the submission. And much more.

The docs are incomplete (still waiting for the community to help with that ) but you can find plenty of  information, illustrations, presets and Dataform enthusiasts ready to assist in the Dataform forum.

hth

Take a look at the solution discussed in the thread Group peer review in the Dataform forum. In that solution you predefine the submission entries to the effect that you can pre-assign problems to students. The illustration is for group peer review but the solution can be set up for individual peer review. At this point the allocation for peer reviews is also predefined and manual but is not too difficult to do and should take not more than a few minutes and a few clicks, even for 250-300 students.

We've already discussed the Dataform in another thread perhaps for a different purpose. The Dataform may offer you a way to meet this requirement. You can post the grades and comments for all milestones in the same activity. For each student, you can use either an entry per grade or a field per grade. The former would allow you a vertical display of progress and the latter horizontal or vertical. If you want to display all these items in the gradebook, you can use the Dataform multiple grade items feature together with the separate field approach. If you want to give this a try, we can continue the discussion in the Dataform forum (https://moodle.org/mod/forum/view.php?id=8192). hth

I'm referring to the "Wake up call or Sigh of Relief" activities. Are these real activities or just place holders for external scores? And what's the purpose of the multiple exports?

Do you really need these activities in the gradebook? They don't actually participate in the grade, do they?