How can this work if there is no Oracle? Think about it, the price of USD/ETH has to be retrieved from somewhere. It's not in the blockchain, so it must provided in an Oracle.
There is not one trusted oracle. The oracles are determined by the MKR holders, and MKR holders can easily replace oracles if they act badly. MKR ownership is decentralized, hence I don't think it's accurate to say there's one trusted oracle.
I agree with you on volatility playing an important role in bootstrapping the network in the early days of digital currencies like Bitcoin and Ethereum.
I think stablecoins will play out differently though and are an important component of attracting new users. I believe decentralized applications will be built that bring mainstream users in, and these users will want a stable store of value to use these applications.
Bitcoin couldn't have prevented the OPM attack, but these types of attacks will continue to highlight the flawed way that institutions store data online.
To each his own. In my mind, spending another 60K to "figure out what I want to do" was the riskier decision than joining a company I believe in. IMO "forging strong personal relationships that could last for decades" does not require you to go to an Ivy League school. Really just requires an internet conection these days.