Is obliged to cross road in difficulty (8)
I believe the answer is:
hardship
'difficulty' is the definition.
(hardship is a kind of difficulty)
'is obliged to cross road in' is the wordplay.
'is obliged' becomes 'has'.
'to cross' indicates putting letters inside.
'road' becomes 'rd' (abbreviation).
'in' becomes 'hip' (both can mean fashionable).
'has' placed around 'rd' is 'hards'.
'hards'+'hip'='HARDSHIP'
(Other definitions for hardship that I've seen before include "Privation difficult to endure" , "Difficult circumstances" , "Need" , "Adversity, affliction" , "Severe discomfort or deprivation" .)