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Web Determinations would be a good approach to this scenario if some of the information is in Siebel and the rest of the information (to meet relevant conditions) can be entered by a user. WD will keep track of the goals and prompt the user for more information until they are met.
If the information cannot be provided manually then you are probably looking at using the Determinations Server and then using code to examine the decision reports of conditions that are not met to determine what information is needed.
The Interview service provided by the Determinations Server is not directly supported by the connector (only assess operations are supported), but the inteview service would not give you any more information over Decision Reports from an Assess operation or Web Determinations.