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The easiest way to do it is to do it the right way with LetsEncrypt. The hardest way to do it is the wrong way, where you create your own CA, import it as a root CA into all of the machines you’ll be accessing your servers from, then create and sign your own certs using your CA to use in your servers.
Yes, LetsEncrypt with DNS-01 challenge is the easiest way to go. Be it a single wildcard for all hosts or not.
Running a CA is cool however, just be aware of the risks involved with running your own CA.
You’re adding a root certificate to your systems that will effectively accept any certificate issued with your CA’s key. If your PK gets stolen somehow and you don’t notice it, someone might be issuing certificates that are valid for those machines. Also real CA’s also have ways to revoke certificates that are checked by browsers (OCSP and CRLs), they may employ other techniques such as cross signing and chains of trust. All those make it so a compromised certificate is revoked and not trusted by anyone after the fact.
All they say that if the private key is stolen then you're screwed. Think about it, if an attacker can:
You have a much bigger problem my friend
While I agree with you, an attacker may not need to go to such lengths in order to get the PK. The admin might misplace it or have a backup somewhere in plain text. People aren't also prone to look to logs and it might be too late when they actually noticed that the CA was compromised.
Managing an entire CA safely and deploying certificates > complex; Getting let's encrypt certificates using DNS challenges > easy;