Has to cross road in difficulty (8)
I believe the answer is:
hardship
'difficulty' is the definition.
(I know that hardship is a type of difficulty)
'has to cross road in' is the wordplay.
'to cross' indicates putting letters inside.
'road' becomes 'rd' (abbreviation).
'in' becomes 'hip' (both can mean fashionable).
'has' going around 'rd' is 'hards'.
'hards'+'hip'='HARDSHIP'
(Other definitions for hardship that I've seen before include "Adversity, misfortune" , "Austerity - affliction" , "Adversity, affliction" , "Physical suffering is a tough vessel" , "distress" .)