<p>Speaking to your workload concerns, one idea might be to send him to a boarding school summer program so he can test the waters and get a whiff of the overall vibe. I know Loomis has a program for middle school students. I think Eaglebrook might too. (Beyond that I know squat re: their specifics.) Dig around and you’ll probably find a lot of options. </p>
<p>Seems to me that could be a decent transition test, from the Waldorf approach to standard boarding school pedagogy, etc.</p>
<p>Bottom line though, I think, is that schools love kids who are alert and articulate and intellectually curious. Traits like those bode very well for what he/she will contribute to the life of the school.</p>