Join with difficulty? (5)
I believe the answer is:
hitch
This clue is a double definition.
'join' is the first definition.
(thesaurus)
'difficulty?' is the second definition.
(I know that hitch is a type of obstacle)
'with' is the link.
(Other definitions for hitch that I've seen before include "Snag - free ride" , "Snag, drawback" , "Setback" , "Hindrance" , "Marry" .)