You're almost there, you want
<xsl:if test="descendant::Item[@ExampleItem='Yes']/descendant::Answer">
It's surprising how often people forget that you can have predicates on any step in a path expression.
You could also write this as
<xsl:if test="descendant::Item[@ExampleItem='Yes'][descendant::Answer]">
or various other combinations for example
<xsl:if test="descendant::Item[descendant::Answer]/@ExampleItem = 'Yes'">
Michael Kay
http://www.saxonica.com/
Author, XSLT Programmer's Reference and XPath 2.0 Programmer's Reference