Homeless one cheered into harbour? (3,4)

I believe the answer is:

bag lady

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'homeless one' is the definition.
(I've seen this in another clue)

'cheered into harbour?' is the wordplay.
'cheered' becomes 'glad' (I can't justify this - if you can you should believe this answer much more).
'into' is an insertion indicator.
'harbour?' becomes 'bay'.
'glad' put within 'bay' is 'BAG LADY'.

Can you help me to learn more?

(Other definitions for bag lady that I've seen before include "Homeless female" , "Vagrant" , "homeless person" , "Homeless woman" , "street-walker" .)

I've seen this clue in the Sydney Morning Herald.

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