Shirker sending one out with repeated hesitation (10)
I believe the answer is:
malingerer
'shirker' is the definition.
(malingerer is a kind of shirker)
'out with repeated hesitation' is the wordplay.
'out' is an insertion indicator.
'with repeated' becomes 'malinger' (I can't justify this - if you can you should believe this answer much more).
'hesitation' becomes 'er' (sound made while hesitating - um, er).
'malinger' going around 'er' is 'MALINGERER'.
'sending one' is the link.
This may not be right. Some or all of it may belong to another bit of the clue.
Can you help me to learn more?
(Other definitions for malingerer that I've seen before include "One feigning illness to avoid work" , "Slacker" , "He's not bad, really" , "I avoided work?" , "Shirker" .)