For the monthly check in, are you looking for something like InkingItOut does? A "tell me how it's going" with maybe a bonus questions maybe like "tell me about something you were stuck on and how you fixed it"? And then a different bonus question every month, which would be more targeted toward the deadline?

For that, I could do the monthly check-in... first weekend of the month (but check in any time) with the last couple as a monthly 'wellness' check to make sure about participation.