Badly damaged position that fails over sixties regularly (4,4)

'badly damaged position' is the definition.
'bomb site' can be an answer for 'position' (bomb site is a kind of position). I'm unsure of the 'badly damaged' bit.

'fails over sixties regularly' is the wordplay.
'fails' becomes 'bombs' ('bomb' can be a synonym of 'fail').
'over' means one lot of letters go next to another (in a down clue, some letters go over others).
'regularly' indicates alternate letters (regularly take one letter, leave next etc.).
The alternating letters of 'sixties' are 'ite'.
'bombs'+'ite'='BOMB-SITE'

'that' is the link.

Can you help me to learn more?