Jotaro

He's lost more than he's ever gained. Especially with the shit he had to deal with when he was just 18

^Yeah and he has to internalize it all because he has to be macho. I bet he's secretly an alcoholic by the time of SO

Jonathan watched his dad die and his house burn down.

Jotaro watched all his friends die, including his mothers suffering and the death of his grandfather and gaining PTSD.

(Who knows what kind of suffering he faced during the years inbetween DIU, GW, and SO)

Yeah and Jonathan died with a smile on his face iirc, which alone tells me he did a pretty good job at dealing with his life issues.

Good point

Jonathan had a peaceful death

Jotaro died thinking he failed his daughter and the universe

^Yes