I agree. Another potential distinction: "Who would you rather be?" versus "Who do you imagine you would be happier if you were?"

I was aiming for a question that would produce a simple status assessment. I hoped halo effect would counteract some of the potential problems with the wording. After thinking about it I decided a rather ambiguous but easy to understand question might best capture this without discouraging too many people from contributing, so yes it was intentional.

But please I have little experience on poll questions and am not a native speaker of English to boot, so please share any further constructive criticism you might have! :)

I couldn't answer for this reason. It's asking "whom do you rate higher [according to criterion X]?" without specifying criterion X.