One other thing I didn't see mentioned, on Sep 29, 2014, CloudFlare (a very popular proxying CDN because most sites of moderate size can effectively use them for free with simple DNS changes), announced the offering of free SSL for all sites they proxy.

Essentially, anyone proxying through them could automatically and immediately hit their site with https:// and it just worked; no changes needed on the backends, nothing to pay for or renew.

For me personally and for many other people in the same boat, this is tipped the scale for me. My sites are all basically personal/hobby sites that I would have liked to use SSL for, but couldn't justify the cost and maintenance time. Often the cost was more about having to use a more expensive hosting plan (or start paying instead of using free options) as opposed to the cost of the cert itself.