The question is whether it is more healthy in the long run to let resellers get away with it or to punish everyone by trying to implement a system that catches resellers.
That's an empirical question, that we don't have a lot of data for directly. We do have a lot of indirect data. On the trying to catch people side: that the current democratic-legalistic justice system is extremely counterproductive in how severely it punishes criminals, that attempts to stop fraud with government social programs typically cost more than the fraud they fights, and that fighting digital piracy negatively affects sales because pirates spread popularity through word of mouth. Meanwhile on the free association side, public libraries aren't robbed empty; community kitchens have plenty of volunteers to get food, pay rent, and clean up; big boxes of Halloween candy can be left on someone's porch and most of the time it doesn't get robbed by one person; lots of countries have self-sustaining queueing cultures; etc.
I don't really know cases of gift economies being tried and failing, but it's possible that it often isn't reported if it happens.
In terms of social predictive reasoning, you could make the argument that openly telling resellers "it's fine if you resell it if you need the money but please donate or contribute if you can, and please tell people about us" is way more effective than turning it into a game of wits where resellers are too busy evading the security system that everyone else suffers under to question whether they're making a morally just decision. For example, it seems harder for an undocumented person to prove themselves trustworthy without putting themselves in harm's way than for a veteran reseller-scammer to fool someone.
In terms of moral red lines, AFAIK many people in this Instance are happy to have seen nothing if someone shoplifts or pirates something. Would it be worse if a reseller takes things from someone who has already decided to give it away for free?
So all in all, I would be very curious about the experiment of just letting resellers take stuff if they're willing to withstand people being sad at them about it.
That's... obviously incorrect? Most important software is open source that was made for free. Most data centers run on freeware. And even with mass consumer facing software like youtube browsers the best options are freeware like Revanced. In academia, the whole concept of academic tenure is based on the empirical proof that professors do their job best when they don't have any obligations and they can just get a basic income to do whatever.
The best way to organize the tech industry is to make copyright and patents illegal and to give everyone a universal basic income.