I'm still only 40 pounds lower than my highest weight, but I've been at both sides of the spectrum, very skinny and obese.
When I'm thin, I miss the cushion that was my butt, and the warmth my fat had provided me. I do also miss being a little more invisible, because I feel that thin me attracts too much attention.
When I'm heavy, I miss my thighs not fighting each other and destroying my pants inner legs, and I miss the energy I used to have, the ease with which I would move my body.
So both sides have their perks and their disadvantages.