This is an upfront cost and is possibly a one-time cost per-agreement.

Practically nobody downloads and installs sudo directly from the project website; people install it with their distribution of choice. The agreement could be automated and included in the licensing process. ie: the license gives specific distributions access to the software (either via paid or other agreed-upon terms appropriate to the distribution) and perhaps individual licensing terms for non-commercial entities.

Of course, the bigger ask in this decade is in use for training LLMs. OSS shouldn't be laundered through an LLM (IMHO) for license avoidance. Maybe some projects are OK with that (eg: many BSD licensed works.) There are some that likely aren't.

> The exact moment you charge for something, you need payment processing, a bank, a legal entity to hold said processed funds, you have liability, you need some sort of marketing / sales process (even if it's just copy on a website),

That seems like an area that's ripe for innovation. What does it take to get setup on a platform like Patreon? Seems like something similar ought to be setup for open source/independent development, probably an idealistic nonprofit.

> and the barrier for someone to use your product is suddenly extremely high, simply because it costs something.

All the organizations who really ought to pay are already setup to do all that, and do it all the time.

> But the core reason why FOSS spreads and took over is precisely why it is difficult to fund. No one is going to pay for something when the alternative is free. And the moment you start to charge some free alternative comes along and your prior users spurn you as greedy

What we need is innovation. Maybe a license that has a trip-wire? If not enough money is voluntarily deposited into a tip jar over a certain period of time, the license requires a modest payment from all for-profit organizations of a particular size.

That's up-front, is for the most part free, and incentivizes some payment.

The code can become "radioactive" as well when a software library goes paid. It starts phoning home with information about its environment to ensure compliance which is just kinda... icky to most devs. I certainly don't want that bloat in my dependencies.

I think you have good arguments, but I wonder if there are alternatives that could work in at least some cases. Like, how Unreal engine's license works. Source-available to game developers, but in theory limited to paying customers, or something along those lines.