The 30,000 songs he purchased are ALL illegal.
Turn him in to the US Marshall. PERIOD! 
He is NOT YOUR friend! 
You may consider him a friend, but it is not mutual with what he has done in your territory.
He is ILLEGAL as are the others and YOU will soon be facing a dwindling market to pay for your services. Act now to stem this illegal tide in your territory.
That's what we are all fighting for; every song purchased and fully within the law. There are a lot of things going on in the industry that will probably bring down the law on bootleggers. Be forewarned in advance.
A major producer is now going after the bar/venue owners as they have assets to loose. He is making it clear that if they hire a KJ with illegal songs, they will pay. We'll see what comes from that, but it is underway in one state now.
Protect your territory from illegal bootleggers. The guy doesn't sound like anyone in this Forum would go to his show a second time. He is NOT an asset to the industry, as you have pointed out.
Sorry for the negatives, but it really crisps me when I hear of the bootlegging going on now.
As to the software he is using, we expect them to be off the market within 6 months.
