As for reasons, there are tons of folks with personal websites on providers that only offer expensive yearly certificate options. Most CDN providers don't support LetsEncrypt. Most shared hosts don't. The Cloud Sites platform for multi-site shared hosting (formerly RackSpace, now at Liquid Web) that I use for a dozen of my friend's sites I host for free doesn't. So, essentially, this means that personal hosted websites either stay 'not secure', get ditched, or increase in price quite a lot. Yes, it's just 5 to 10 bucks a month to spin up another instance on Digital Ocean, but it's yet another 'server' to manage when I'd rather decrease the number than increase it.