I experimented with LetsEncrypt a few months ago, and found the process to be VERY manual. This was on a bog-standard Debian install running common web software (lighttpd) with a few vhosts. Certbot does not seem to support lighttpd, so it's: download this third party script, run this, copy that, run this, cat these files together, restart the web server process, etc. Sure, that can all be cobbled together with your own mega-script, but at that point, you start just looking for another provider (which OP did). If I were not as comfortable with the command line as I am, I'd have found the initial setup to be daunting, let alone automating it.
Re:Rate Limits
by JoshTriplett on Wednesday August 17, 2016 @01:59PM
(#12306740)
Even better than certbot supporting it would be if lighttpd supported ACME natively. You might file a feature request with lighttpd requesting native ACME/LE support.
Those aren't really an option for me, I use shared hosting without command line access. I realize this is an issue specific to my case but I know many other people that have their own small sites running on similar hosting as mine.
If continuing to use your current hosting provider is important to you, I suggest you ask them to integrate Let's Encrypt on their end. (That could include just letting you get Let's Encrypt certs through cPanel; it doesn't necessarily have to mean a lot of coding for them.) We've been talking to a number of providers of various shapes and sizes who are doing this or planning to do it. It's the best option for hosting environments where the customer doesn't have administrative access.
Your web hoster should integrate a way to automatically get certificates. Many already do. If they don't offer that you may want to consider using another webhoster.
If you have it scripted in a vm, I think that you should set up a vps that turns on every month and runs it.
You shouldn't do anything by hand to renew certificates. The short certificate lifetime encourages you to automate the process.
Clients exist for Windows, and web servers exist for Windows that include native support for ACME and Let's Encrypt.