I've spent way more time than I should have reading about this...
The Dashcon thing is the worst managed convention I've ever heard of. And that has some serious contention.
There's a huge
eye melting pair of posts that go into the origins and "organisational structure" (to use the term very loosely) of the con. They basically had little to no organisation, no effective central leadership or decision making, used completely random volunteers as parts of committees with no defined goals, failed to share information and didn't seem to have clear answers to any questions posed by those committees, and then you mix in all the usual drama of tumblr fandoms (seriously, it's not the social justice stuff that's the weirdest parts of tumblr, it's its place as the new Liverjournal, now with more gifs and easier to find shit that you find enraging and must rant about).
That seems to have been reflected in the con itself. There are some questions over whether they were legally registered as a company in the state it took part in, and whether that would make the con as a whole illegal or not. There have been claims that security was lax to non-existent (significantly claims that age restricted panels were laxly policed).
The big money thing seems to have come from their not coordinating well with the hotel. I don't think the hotel was at any time told what they were there for. That lead to them demanding the balance of payment on the first day rather than at the end of the con, making them pay up $20k out of pocket. The organisors only had $3k on hand, so they had to hold a fundraiser to get the other $17k.
It sounds like Night Vale was a similar problem, although that's murkier. The claim is that they demanded money up front and wouldn't wait for either of the payment options offered, although that doesn't sound especially likely given the circumstances. Similarly a lot of invited guests found their hotel rooms were not paid for, although these are being reversed (if I had to guess, they probably diverted the funds to the hotel's demands and paid back with the funds originally expected to pay for the hotel from the second/third day stuff).
Most of the rest was just a matter of having no funds and no real organisational force behind it. Given the way the 'committees' worked it's hardly a surprise that guests didn't turn up and that there were no real resources. For a convention with literally zero organisational background, it was... still a complete fuckup but only of questionable legality? So could have been worse? Maybe?
I do believe (some) people enjoyed themselves. People have a tendency to do that. Strange as the thought may be.