Ideally even separate certs for every subdomain, but as Let’s Encrypt has cert limits, and I want to avoid SNI in the future, I’ll probably have to use wildcard certs.
SNI transmits the host unencrypted, that is a real security issue.
Systems that hostname their customers (mycompany.example.com) should use wildcards for that scenario instead of SNI, among other reasons. That’s the only possible concern I can imagine.
Multi domain certs help but then you need to encode all the names ahead of time and if you miss a name you need to reissue and reapply the cert.
Otherwise an adversary could simply see what IPs you connect to and reverse DNS them.
Back dating with a technical rationale (e.g. to work around crap clocks and historically as a way to hide more entropy near the start of the signed certificate) is accepted in the Web PKI, it is only forbidden to use back dating to try to dodge Baseline Requirements, for example back dating to avoid the restriction on SHA-1 after 2015 was prohibited and is one of the things StartCom / WoSign were caught doing.