Can
I purchase one SSL cert (a wildcard cert) to cover A and B, or do I
need to go about it a different way? From what I understand, wild card
certs will work across multiple machines, but I would like to get some
confirmation of my strategy.
Yes, wildcard certificates can work across multiple machines.
If you don't care about the brand name on the certificate, take a look
at the ones from RapidSSL. We use them ourselves for in-house stuff.
$199/year.
GoDaddy also offers the same product, with larger discounts for
multi-year purchases:
Pay close attention to the details. Some wildcard certificates in the
market only allow multiple subdomains *per server* and you have to pay
an additional fee per each additional server in use.
For example, DigiCert sells the same product as RapidSSL for the
inexpensive wildcard offering... except DigiCert charges $450/yr. Both
provide unlimited subdomains on a single domain, on unlimited servers.