So some completely unknown guy with almost zero connections can raise two grand for a module but springing for a lawyer is totally out of the question?
Again I'm not seeing the problem with keeping out the riff raff.
It was closer to $1880 after Kickstarter fees. Likely $1500 after taxes if he was smart enough to leave a buffer. He also had to pay any artists, which isn't cheap.
And he's not entirely unknown: he did two other adventures people could buy to see that he was able to deliver on his promises, one of which is selling well on Drive-Thru. And it was his second Kickstarter. His first raised less:
https://www.kickstarter.com/projects/442231682/5th-edition-dungeons-and-dragons-beneath-the-razor. That one made $690. Or $540 after everything.
And from the look of the sample pieces, he didn't consult a lawyer as his statblocks are a little too close to WotC's in format. If he had talked to a lawyer, he'd have likely lost money from his first Kickstarter and just be out of the hole. Heck, the risks section of the Kickstarter don't even mention the risk of WotC shutting things down, so I'm not sure how aware he is of the OGL.
Otoh I don't get out of bed for less than about fifty dollars an hour so I'm really not going to try to publish anything.
And that's the catch. Your standards are higher than freelance standards. Heck, they're high for most professions as the average hourly wage is under $30/hour. That's gonna skew your perspective.
Especially since, when making $50/hour (or higher) a $1000 legal fees tab is managable. I make under $25/hour and work short hours, so a $1000 legal fee wipes out most of a paycheque. With budgeting, that's five months of saving to even consider the option and involves me not buying any new books or going to the movie or generally spending anything on non-essentials.
Making D&D content shouldn't be exclusive to the wealthy. You shouldn't need a loan to get started. It shouldn't be comparable to starting up a full-time business.
Especially since we want to encourage you people to get invested in the game.
Especially not these days when anyone with a computer can self-publish.