I played with Caddy a little and had an SSL for a domain I already have one for without even asking for one.
Is this not a problem?
Normal DV certs are either "add a CNAME, upload a uniquely named html / txt file, or click a link in an email" -- you've already done one of those (automatically in caddy)
Lets Encrypt asks one question without you having to deal with it - the question where you prove you own the domain by placing a file in the webroot. This is just as much proof as the email verification you get from existing strategies. Except it involves less headache, because you aren't ordering from namecheap, then getting emails from @comodossl.com that fail SPF checks asking you to click links.