@Korbyn - while it does complicate things, there shouldn't be an issue. The company should be able to use a public DNS name that does work, that they can get a real cert for, and they should be fine. Having a non-public internal namespace is not really common, but there are organizations that have that.
@Kimberly - you could use any email service provider that has a web interface and just share the password with your husband. Think Hotmail or Google or Yahoo. They are all free.
@rikiros - Hmmm... Thought provoking, as always. Keep those interesting comments coming!
@Bob - Wildcard certs can be used in just about any situation. There are some issues with Windows Mobile 5.x clients and wildcard certs, and some non-patched Windows/Outlook versions, but those clients are so old that usually they aren't an issue any longer. The main problem with wildcard certs is that administrators tend to leave the cert files "laying around" on their servers (I tend to do so in a "c:certs" directory), and the security guys just don't like that. With the wildcard cert, you can act as any server name in that org that you want. PLUS, wildcard certs tend to cost a lot more from cert providers...