Think that 1930 is a good estimate for this photo.
Left is Holt's Wharf, then Signal Hill with (I guess) Signal Hill Battery/Blackhead Fort. The tower has its cupola, so its definitely between 1928 and 1933. Can't see the lighthouse.
Right of the hill are houses, likely DeJongh family residence, and then buildings under construction: Lyemun Flats / Lyemun Buildings / Harbour View Hotel.
Any other suggestions are welcome.