The B&R silent issue made me cry. I'll admit to that. ...I had to sit on the loss of Damian for a long time.
During DC's 2007-2008 series '52' you see Vic Sage as The Question basically wither away and die from cancer. That was really tough for me, cancer has hit my family hard over the years.
Losing Peter Parker in Ultimate Spidey was such a tragic ending too, made it really hard to open up to Miles for an extended amount of time since it just felt wrong to replace the Peter I had literally grown up reading.