http://technet.microsoft.com/en-us/library/bb125165.aspx – How to prepare certificate request
http://technet.microsoft.com/en-us/library/aa995942.aspx – How to create certificate for mutiple hosts and how to configure certificate for specific service in Exchange 2007
http://technet.microsoft.com/en-us/library/bb201700.aspx – Modifying Outlook web access on Exchange 2007

It is possible that dedicated servers come in a cheap web hosting deal. However you might need to make certain compromises where the web design or the domain name registration is concerned.