I think part of their problem is that they built their platform on top of WordPress. But they obviously chose WordPress as their software engine for a good reason.
But of course, if there is a nasty WordPress bug, it takes some time to track it down and fix it without disruption. I hope they are using a dedicated cloud for this (like AWS) and not a hosted service.
I'm in software, which is why I notice these things. But overall, I am rooting for them big time. Heck, they are even sending out emails for one on one time with the founders. I bet Medium didn't do that when it lifted off.
That goes to your main point in your story and then some. It's not just a ground floor opportunity, but it's a chance to encourage a group of people who understand the writing process and want to at least try to come up with a rewarding platform. I'll tolerate some growing pains for that kind of attitude.