Do you think Steinberg is really broke, or is he just crying wolf?
I personally think he does not have much money, but the whole thing is rather puzzling. I can only give my opinions and impressions:
His bankruptcy filing from 2016 reveals he reported income (for himself and spouse I believe) then just shy, iirc, of $2,800/month. Most of that was Social Security, so would not be taxed.
I think the assumption most spectators of Gene make is that he was reporting something like his revenue from podcasting et al in that declared monthly income, but not including the donations he receives. The donations dollars are assumed to be variable.
The bankruptcy DID include a lot of loans, including at least one sizable personal loan, suggesting to me Gene tends to burn through cash as fast as he lays his hands on it. If I'm not mistaken he's freely admitted to entering into deals such as expensive car leases due to his bad credit, and him wanting a better car to drive.
Many times though if one reads his cash appeal emails carefully, it seems clear he is hoarding some cash while putting off bills and begging for cash to pay other expenses. For example he'll say he must have $700 to pay his car insurance by 5 p.m. on a particular Friday afternoon, then on Monday morning note in passing that he managed to pay the car insurance. And he's made references to a "cash reserve" before in those emails.
I believe that right now he is trying to save up to be able to afford a new apartment, so I don't think that he is 100% broke. There seems to be something pathological underlying the begging and some of the other self-destructive behavior, so it wouldn't surprise me if he's hoarded more than he is letting on. Still, hard for me to believe he'd spend months in a motel room if he had better options.
As an observer from a distance of Gene, my impression has been he tries to avoid paying for anything until he absolutely has to pay for it. Nothing wrong with that necessarily, except I think he pushes it and it winds up getting him into trouble - for example, serial evictions from apartments. Also - again just my impression - he doesn't seem good at budgeting, which you need to be in order to play that kind of "pay late" game successfully. It seems to gall him to have to pay for the necessary routine expenses of life. And you can pretty much count on him making things sound worse than they are in the begging emails. He has to make them sound like a desperate appeal, with some little ray of hope for the future if you'll help him past the rough patch.