Awarding Points http://www.experts-exchange.com/help.jsp#hs=29&hi=407
Trusted SMTP relay http://blogs.technet.com/sbs/archive/2008/09/18/how-to-configure-trusted-smtp-relay-in-exchange-on-sbs-2008.aspx
Alias's, just add whatever you want as far as email addresses go for each individual. There is no tool I am aware of which allows you add multiple smtp addresses for a user or multiple users.