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Have you check the Apache log from Server Admin application to see if there are errors in starting automatically? When you mention starting manually, are you doing it from Server Admin or from command line to start apache?

Is your router set up for WEP or WPA (which is the security for the network)? If you are not sure, check 'Properties' for your network card on the Windows lapotop. If you set up the router and have admin access to it, you should be able to see in the Wireless settings if it is set for WEP...