> How would one know what to recommend while knowing nothing about `jcurbo`s intentions/designs/requirements?

For someone learning Python? Just give them your best suggestion. Look, it's fairly easy.

Learn Python 3. There are differences, and you might run into issues later on, but once you get to that point, you'll know enough to do something about it.

See, when someone asks whether to learn Python 2 or Python 3, that's what they are asking for. If they are learning for specific reasons (for a job, lets say), then instead of trying to answer, you ask follow up questions. But for learning a language, they are seeking advice from experienced people.

So, when those same experienced people, who already know Python 2 and/or Python 3 tell them to learn Python 2 and/or Python 3, they are being told: we don't know.

And how is someone inexperienced supposed to know which one to learn when experienced people don't know?

Basically, if you can't answer the question because you feel you lack information, ask. Otherwise, answering the question "Learn Python 2 or 3?" with the answer "Learn Python 2 or 3." isn't helpful.