I'm curious what the benefits are of paying for SSL certificates vs using a free provider such as letsencrypt.
What exactly are you trusting a cert provider with and what are the security implications? What attack vectors do you open yourself up to when trusting a certificate authority with your websites' certificates?
In what way could it benefit security and/or privacy to utilize a paid service?
And finally, which paid SSL providers are considered trustworthy?
I know Digicert is a big player, but their prices are insane. Comodo seems like a good affordable option, but is it a trustworthy company?
Not the only use cases, but you'd need a different service if you need/want wildcard certs, certs that are manually installed and managed, or certs with a longer expiration.
I'd say they're actually easier, at least in my experience. Since wildcard certs use DNS-01 verification with an API, you don't need to deal with exposing port 80 directly to the internet.
You can also delegate a subdomain to another provider with an API, but yes I see what you mean. Although I feel like getting port 80 open would be difficult as well in those situations.