Hardest thing to understand when I first got introduced into this whole Bitcoin thing was how addresses / wallets worked. Not in the sense that I didn't know to operate them, but in how they operated and why they operated in such ways. (Paper wallets / QR codes / Also even the Blockchain : those kind of stuff always made me curious)
:: My easing into Bitcoin wasn't that rough and actually was quite smooth even invigorating that I can finally now partake in online activities without the need for a credit card. However easy it was getting INTO it, understanding it was a whole other thing.