The certificate for *.company.org will only work on a domain where the * is replaced with a name.
Putting www infront of that name makes it a second level ie ..company.org which is why
the certificate errors appear.
Certificates for ..company.org are not available, to the best of my knowledge.
A wildcard will only work on one level *.company.org
I am not sure how you will get around this in your examples.