I saw the Aaron Boone homerun - I saw the ball roll through Buckner's legs - and then lose Game 7 to boot! (as an 8 year old) There was Bucky Dent when I was too young to notice. When Boone hit the homerun it was the first time I thought they would NEVER win.
That said, that was all before two titles in 5 years, one in literally the sweetest way possible. Honestly after 2007 - and hell, the courageous almost comeback in 2008, I stopped having my summahs ruined. The collapse in 2011 was bad (and thank God I don't live in Boston anymore for something like that) but it is hard to have any sort of moral authority to whine anymore.
As Bob Ryan said, the last decade of sports in Boston is the good old days of the future for folks my age. It is hard to get that crushed or angered by the non-victories.