WPF Datatrigger not firing when expected

Alternatively, you could replace your XAML with this:

<TextBlock Margin="0,0,5,0" Text="{Binding ElementName=EditListBox, Path=SelectedItems.Count}"/>
<TextBlock>
    <TextBlock.Style>
        <Style TargetType="{x:Type TextBlock}">
            <Setter Property="Text" Value="items selected"/>
            <Style.Triggers>
                <DataTrigger Binding="{Binding ElementName=EditListBox, Path=SelectedItems.Count}" Value="1">
                    <Setter Property="Text" Value="item selected"/>
                </DataTrigger>
            </Style.Triggers>
        </Style>
    </TextBlock.Style>
</TextBlock>

Converters can solve a lot of binding problems but having a lot of specialized converters gets very messy.