You could also set up a blog for you both to post to and comment on. Set it to private (only you and he can access it) and use it for:

1) Him reporting on his day/writing his journal. You can do this daily, weekly whenever
2) Him reflecting on his thoughts and feelings
3) Him being allowed to feedback on tasks you set him - both reporting the results (and you can attach photos or even video to most blogs) and him telling you what he thought about the task
4) You assigning him tasks for him to complete
5) Your thoughts and feelings about the relationship so far
6) Your feedback to him about how well/badly he completes tasks and assignment of punishment/reward tasks.

A blog is a little more 'formal' than an e-mail and so he may feel more inclined to write more. Also, making it once a week to report allows him to schedule it better around his other life.