"At run time, the authorization module iterates through the allow and deny elements, starting at the most local configuration file, until the authorization module finds the first access rule that fits a particular user account. Then, the authorization module grants or denies access to a URL resource depending on whether the first access rule found is an allow or a deny rule. The default authorization rule is . Thus, by default, access is allowed unless configured otherwise."
Article at MSDN
deny = * means deny everyone
deny = ? means deny unauthenticated users
In your 1st example deny * will not affect dan, matthew since they were already allowed by the preceding rule.
According to the docs, here is no difference in your 2 rule sets.