If you "feel bad for him", you are not looking down on him.

If you "feel bad for poor him", you are referring to him in a way that implies his position is lesser.

"Poor $noun" is nearly always derogatory towards $noun. Off the top of my head, I can't think of a neutral or positive use for "poor $noun".

Verbal communication is imprecise enough that people will overlook "poor $noun". In text, you have the opportunity to proofread and revise your statements, so "poor $noun" drastically changes the meaning of the phrase.

You're formalizing some kind of culture disconnect. If I say, "Poor John lost his dog." to any native of the Gulf Coast, no one is going to mistake that for an expression of superiority to John.

It comes down to the context: yes, when poor John loses his dog, we can all understand, what you meant. However, Stallman did not lose anything, furthermore, he is successful and happy with his choices, therefore your "poor Stallman" comment is by definition condescension.

Nothing but respect here for RMS. Successful: yes. Happy with his choices: debatable. His writing and his countenance don't really give off the "happy" vibe.

Perhaps the condescension in my writing (of which there was none) was not so much in the signal as it was in the receiver? Your reply is absolutely dripping with it, window-dressing a cry of "is not / is so" with: "however", "furthermore", "therefore", and "by definition."

The only thing that would have made it worse would be putting it into pseudocode!