We were trying to decide what is the best approach to get SSL certificates installed on our platforms. One option, of course, was to buy a certificate, manage it, install it manually, fight all the issues, etc...

Eventually, decided to user the certificates from CloudFlare. It is free!!! no need to manage it yourself, which makes it super easy and hassle free. In terms of installation, since all of our stuff in on DigitalOcean, the easiest way to install the certificates was to terminate them on LoadBalancer. Again, the setup is really easy, and no need to manage anything on your origin host side.