Barring some unexpected cooperation from my hosting provider, my HTTPS rollout will be delayed. They have not rolled a management console for SSL certificates, and it’s not even on their radar for the basic hosting package.
My options going forward are to pay $20 a month for VPS with my current host or bolt, probably for Amazon Web Services, I’ll bet I can get under $20 easy. Since everything is going to break either way, I’m leaning toward the latter. If any webdev types have some other thoughts on good WordPress hosting companies that support SSL and multiple domains, I’m all ears.
Let’s Encrypt covers just one piece of the puzzle — getting a universally-recognized certificate. Unfortunately, it can’t cover for everything else, especially if you have a web server stuck in 2008.