Keyword based email replies

[crazy4laptops]

arrrrgh, google is of no help here :P
all the results are pretty much marketing/mass mailer shareware (yuk)

im looking to start my own automated helpdesk on my website...
csg.hereweb.com

it will be email based for simplicity reasons... automated ICQ chat isn't my strong point

however, i can't find any free software to test my idea for practicality :P

outlook 2007 and 2010 require too many mouse clicks to set up keyword responses, and i cant add and/or operators which would simplify many things
i have to make a separate outlook filter for each keyword or phrase
and that is so tedious that the payoff is negligible
(if i missed a process that makes outlook templates/filters/replies simpler, please let me know)

so my question becomes, would this be easier with a database plugged into an email client? If so, whats the best (simplest) way to set that up?

os choices- windows xp pro, win7, server 2003 & 2008 R2, ubuntu or fedora linux
email clients- outlook, thunderbird, postbox, suggestions??
database- access 2003/2007, mysql, sql server 2008, suggestions??


i've posted this same q on pcworld a while back and didn't make any progress
ref- http://forums.pcworld.com/index.php?...based-replies/

any insights would be amazing

thanks
-C