Vlad, rules must be activated before they can be executed. Activation happens when facts are inserted/updated/retracted into the session. Maybe your case is that nothing happens before the Rule#2 is entered?
You could give a try with a onExit script for you human task node that will make any modification to the session, for instance insert a fact.
<extensionElements>
<tns:onExit-script scriptFormat="http://www.java.com/java">
<script>kcontext.getKnowledgeRuntime().insert(kcontext.getProcessInstance());</script>
</tns:onExit-script>
</extensionElements>
That should activate agenda and when process enters rule task it should have rules ready (of course if the rules condition will be satisfied). I am not a big rules expert so ...
As for the listener, take a look at: org.drools.event.AgendaEventListener an example usage of it can be found here, to trigger rules execution (of ruleflow-group) as soon as they activated.
HTH