Free Let's Encrypt certificates, renewals and custom certificates.
Yes. SrvYard gets Let's Encrypt certificates for you. They last 90 days and SrvYard renews them before they expire, emailing owners and admins if a renewal does not go through. See Get a free Let's Encrypt certificate and How renewals work.
Nearly always outside SrvYard: the domain's A record does not point at the server yet, port 80 is closed or redirected, or Let's Encrypt has asked you to wait. SrvYard checks the DNS records first and names the culprit. See Find out why a certificate failed.
Yes, with DNS validation. SrvYard adds a temporary TXT record in Cloudflare, so the domain's DNS must be hosted there. HTTP validation cannot issue wildcards. See Wildcard certificates with DNS validation and Connect Cloudflare.
No. SrvYard cannot ask your authority for a new one, so you replace it by hand before it expires. The key must be in PEM format without a passphrase. See Install a custom certificate.
It redirects every HTTP request to HTTPS and adds an HSTS header. Too many redirects usually mean a proxy such as Cloudflare in Flexible mode talks to the server over HTTP. Make it connect over HTTPS. See Force HTTPS and HSTS.
Not yet. The new name is not on the existing certificate, so request a certificate again with the new name ticked. Until you do, visitors to that name see a certificate warning. See Get a free Let's Encrypt certificate.
Yes. SrvYard waits, for up to about ten minutes, until the name resolves to your server and then requests the certificate itself. You only need the article for your own domains, wildcards, or when that automatic request failed. See Get a free Let's Encrypt certificate.