I am here to answer any questions for you guys.
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Any student/alum/parent/friend can answer questions about Hill. Do not ask “chance me” questions; there is a different forum for those.
YAY!!! His Big Brother has been doing a pretty good job of answering HIS questions (If you are he, Thank you!), but I still have a few that come up occasionally. Like…will he find out his roommate before school starts? Do most boys carry backpacks or messenger bags, or nothing? What about the basic supplies, like folders and notebooks? I assume you all still need those, but how many? Best/worst teachers? Any really fun, not to be missed classes? Dutch or Dell? What’s one thing you brought but wish you didn’t, and one thing you didn’t but wish you did? I’m sure I’ll have more. 
Roommate assignments should come September 3rd. Most boys carry backpacks. Herschel brand is the most popular. Notebooks are fine but most kids use their iPads or laptops to take notes. Nearly everything we do academically is done on the iPad, so notebooks aren’t that necessary. But just in case, get 2 or 3. If need be, he can always buy more. All the teachers are great, but it really depends on subject to subject. I really liked the war classes, and I loved economics. Economics has a great simulation project, where you get to manage your own investment portfolio. Between Dutch and Dell, they both have a great “family” environment, which can help a lot as a 3rd former. But Dell Village is newer, with a little better facilities. My family went out and bought everything on the list, including all the furniture. I don’t recommend buying a huge chair, it takes up too much space, especially if his roommate gets one too. I recommend a bean bag chair or something like it. And the packing list is pretty inclusive of everything, but I do recommend extra sheets, and definitely get a mattress top. They make a huge difference. Try to coordinate with his roommate, it will make it a lot easier.