It's an easy box to check to pretend to offer HTTPS so you don't get penalized by Google. Before Let's Encrypt there was no free way to get a legit cert for your cat blog. Faking it via Flexible SSL was the next best thing.
This is false, there have always been ways to get a free DV cert, lets encrypt made it easier
Furhter before Lets Encrypt you would not have gotten dinged by google, Google only went that path when wide spread DV Certs where freely avaliable
Further still, the minor costs per year to get a paid DV cert should be factor when choosing to host your own content versus paying a 3rd party to do it, many of those 3rd parties provided SSL as part of their services.
There is zero need for a Man in the Middle for SSL,
It's an easy box to check to pretend to offer HTTPS so you don't get penalized by Google. Before Let's Encrypt there was no free way to get a legit cert for your cat blog. Faking it via Flexible SSL was the next best thing.