By the end of Season 6, he's been stabbed in the back in All Hell Breaks Loose Part 2 in Season 2, he gets struck by lightning in Wishful Thinking in Season 4, Anna stabs him in the stomach in The Song Remains the Same in Season 5, he gets shot by angry hunters in Dark Side of the Moon in Season 5, and he falls into Lucifer's cage in Swan Song in Season 5. So he has died 5 times so far if I counted them all correctly.
Nope Sam gets him out of it! :P
She died on November 2, 1983 when Sam was 6 months old.
No they do not. Sam is about to go through with the last trial, but the Dean finds out that Sam will die if he does, so Dean stops Sam. As of now in the show, the gates of hell are still open.
Godfrey of Winchester died in 1107.
Ealhmund of Winchester died in 805.
Eadmund of Winchester died in 833.
Benjamin Winchester died in 1901.
Cyneheard of Winchester died in 749.
Elhanan Winchester died in 1797.
Æthelheard of Winchester died in 759.
James Winchester died in 1826.
Cyneberht of Winchester died in 801.