I think you guys are overthinking it. Nana just wanted to go somewhere where he could get drunk while the dregs of his fanbase told him he's great and still hilarious. The last 9 years have shown that he doesn't care/doesn't know how to grow his subscriber base or make money so why would he try to start now? He's just an alcoholic old faggot who craves the adulation of strangers.
It is hard for me to put myself in the shoes of a 65-year-old closeted alcoholic to be fair (mommy's shoes). You also have to figure that Anthony is likely driving drunk again if he is indeed driving himself to and from these bar and comedy club shows. Either that or hiring a driver for these long commutes which means he is burning more cash from each gig. Does he even have a license?
But you also have to remember that Anthony booked a worldwide media tour for his book signings which went nowhere. Thinking that tens of thousands of O&A fans and right wing individuals would flock to his autograph appearances and purchase shelves of his books. He must know that deep down inside he is not a draw on his own. And must book himself alongside mediocre hacks and leech off of their audience more than they are even leeching off of him. Comedians used to do anything that they could to get on O&A for plugs. Being humiliated like Richard Jeni or Birbiglia and so on. Now Anthony has to beg unknown road hacks and has-been losers for pennies.
If you had told the average O&A fan in 2004-2013 that Anthony would be abandoned by Opie, Norton, all O&A comedians, would be destitute, a total pariah, outed as a boy lover and tranny enthusiast, and hated by all of the fans you would have been met with total disbelief. I would just love to once hear from like Terry Clifford, Scott and Todd, John and Jeff, or some other Jocktober victims.