I started watching financial audit on youtube, and now I'm just imagining Dante going onto the show and cannot decide who is funnier to go with him.
Like, Vergil's obviously an option. Caleb would be like, "So you're two brothers in your forties... and neither of you have steady jobs?" Vergil would constantly make excuses and just display that he doesn't understand how credit cards work (he probably thinks they're magic.)
Trish is another option because then the relation is even weirder, "So she's a clone of your dead mother, who became your business partner, I'm just going to call her your sister."
Nero would be the one to have forced him on the show, and wouldn't know the ins and outs of Dante's debt. I think the joke there would be, Dante reveals that almost all of his debt is in private loans from Lady, who technically charges him interest, but is also a partial owner in his business (and his legal wife if I were making this a ship fic, which I likely would) and has been investing in retirement for him, so his financial situation is more that of a man with an allowance rather than the dire straits Nero thinks his uncle is in.
Still the cost break down of "Strawberry sundae, strawberry sundae, pizza, pizza, strawberry sundae-- are you a grown man or a child?"
I think Dante would find it all funny in the latter situation, because I'm convinced he lives like that by choice, and just doesn't care enough to be financially responsible. Although in the former two I could see him getting mad at Vergil and Trish for maxing out his credit cards (when he was the one who wanted to max out his credit cards!)
Also in the Nero version I think it would be funny if it turns out that Nero does not understand taxes because Fortuna has 'tribute' and was accidentally committing tax fraud (Nico would be knowingly committing tax fraud).
I'll need to watch more Caleb Hammer to get this right haha.