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.