Regarding the certificates, if you don’t want to set up stuff on clients manually, the only drawback is the use of a wildcard certificate (which when compromised can be used to hijack everything under something.example.com).
An intermediate CA with name constraints (can only sign certificates with names under something.example.com) sounds like a better solution if you deem the wildcard certificate too risky. Not sure which CA can issue it (letsencrypt is probably out) and how well supported it is