It it possible to have multiple ReWrite rules that all do the same Action, for an IIS7.5 webserver?

You need to match every request, and then use conditions to filter it to just your specific URLs:

<rule name="Old Site = Image1" stopProcessing="true">
    <match url="^(.*)$" />
    <conditions logicalGrouping="MatchAny">
        <add input="{REQUEST_URI}" pattern="^(.*)image/aaa.gif$" />
        <add input="{REQUEST_URI}" pattern="^(.*)image/bbb.gif$" />
        <add input="{REQUEST_URI}" pattern="^(.*)image/ccc.gif$" />
    </conditions>
    <action type="CustomResponse" statusCode="410" statusReason="Gone" statusDescription="The requested resource is no longer available" />
</rule>