Ill-defined situation, with major cut covering disastrous year (4,4)
I believe the answer is:
grey area
'ill-defined situation' is the definition.
(I've seen this before)
'major cut covering disastrous year' is the wordplay.
'major' becomes 'great' ('great' can be similar in meaning to 'major').
'cut' means to remove the last letter.
'covering' means one lot of letters goes inside another.
'disastrous year' becomes 'yare' (I can't justify this - if you can you should give a lot more credence to this answer).
'great' with its final letter taken away is 'grea'.
'grea' placed around 'yare' is 'GREY AREA'.
'with' is the link.
Can you help me to learn more?
(Other definitions for grey area that I've seen before include "not properly marked out" , "One of undefined boundaries" , "Where things are not black and white" , "One of unclear boundaries" , "concrete jungle?" .)