Hey, thanks folks for the responses. Sorry it took me a while to respond myself...
this is really the very first time I've felt ds had any opportunity to stretch himself time-management wise (for school), so I didn't feel too bad that the whole thing was orchestrated by me.
I did have a mid-way discussion of some not-so-ideal decisions (procrastination) but will try to chat again about the whole thing and how it worked/didn't work.