I'm putting my vote in the hat to have the response required box unticked by default (or at least maybe make that a settings option).
I keep forgetting to uncheck it when sending a follow-up for a purchase. I always send a message after I see that the package has been delivered so that I can request feedback or let the person know to contact me immediately if there is any issue with the order. Bricklink has a drive-thru setting for doing this sort of thing automatically with a template (don't see a similar option here though). That would take care of this issue as well.
For what it's worth!
Comments
Customers are notified with a presetted notification here as well when an order is shipped, it is currently not 'editable' however. Personally I always put a small note together with the order to request contact in case there is a problem with the order and pointing out to the feedback system.
'Begging' for feedbacks trough e-mailing has never worked in years, so quite pointless to 'fish' for them. Let the buyers do what they like in those regards ;-)
I would rather be slightly "inconvenienced" than to miss a response required.