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Simple supply and demand, no one is making anyone purchase anything at the inflated prices. If you want to pay retail wait till its in stock. Its not luck that some finds the highly coveted items its almost a job, you have to find out when stores get their shipments and show up at the store(s) at the right time. I've been on both sides of the fence and it does suck when you're on the paying higher prices end of it.
 
1) Check the top of your own screen shot. URL ends in .ca. That's Canada.

2) Now check Apple's Canada store: http://www.apple.com/ca/shop/product/MK0C2/apple-pencil-for-ipad-pro and http://www.apple.com/ca/shop/product/MJYR2/smart-keyboard-for-ipad-pro.

3) Pull out calculator. Do the math.

Do you think they're a bit douchey for trying to make extra money off selling something that's in short supply? Or is it just the free market and who cares?

Personally I think it's a bit douchey. If I bought a pencil or a keyboard and decided I didn't want them, I would feel lucky to just sell them for what I bought them for. But to actually charge more for them than I even paid? Why the heck would I do that? The thought would never even occur to me. I don't know. Just thinking out loud here
 
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