Dear Mike,
I've taken a look at the site you provided access to and I could not understand fro instance how you have set up the manage listings page for the advertiser.
Nor in the same site I can see the contact advertiser button or form in the listing page.
That is why I'm explaining how things are set/configured in the original reference site.
For example if I go to the My ads list page in your test site ( that I can locate from the WordPress admin ) I get several broken shortcodes. What makes me think that somehow the code or functions needed for the Toolset Classifieds site aren't being used.
Regards,
Ana