Dave, I know you’re talking about caring from a slightly different perspective, but if you don’t know Nel Noddings’ work I would highly recommend it to you (e.g., http://infed.org/mobi/caring-in-education/).

A few years ago we had a student look at caring in online learning for her dissertation (specifically, she looked at the Open High School of Utah) – http://scholarsarchive.byu.edu/etd/3355/. You might find something interesting there as well.