As nice a guy as this blogger probably is, he's the bane of services like WPEngine. There is no way to service the needs of his complex edge case of a system for anything like $250/month. They are guaranteed to lose money on him, and the only hope they have is to convince him to leave the service as rapidly as possible to avoid being sucked into the time sink that dealing with him is going to become.
This is the reason you have a "refund" button on the customer page of your admin console. A quick email apologizing for not being able to meet the needs of his unique setup and a refund of his payment, as soon as it became apparent just how impossible things were about to become would have solved this completely.
Or at least one hopes so. The tough thing about dealing with toxic customers is that they grow on you slowly and you don't notice at first. Then one day you realize you've spent four hours just digging into issues and writing emails to this one person who you're probably going to have refund eventually anyway.
I've never met the guys on the WPEngine team. But I feel for them after reading this.