It is difficult for me to say something negative about someone who seems to be having a hard time for a long time. Even if this someone deserves it.

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It might depend on the someone you’re saying something to.

No, not really.

For me it’s easier to say something negative about someone to someone who knows me but doesn’t know them.

I understand. I'll probably smile at the comment if it's funny, but I can't make that same comment on my own if I feel or think that someone else might be having a hard time.

A comment can be a comment without becoming a judgment.

I think is apocryphal but I think is valid:

“Great minds discuss ideas; average minds discuss events; small minds discuss people.”

—Eleanor Roosevelt

I don’t know if that’s a compliment or not…

Neither