i lived in darling habour for a few years and the easiest places to pick up there would be
The Star casino ( watch out for hustlers, they are very slick) it has clubs etc.. onsite and you can game women on the gaming floor
Pyrmont Bridge Hotel - full of tourists and easy lays ( i lived close by so my logistics were great)
King St Warf - Multiple pubs like bunglo8, The Loft etc...but more prone to entitled princesses however lots of 7's and above
Pontoon - easy women abound, in fact most of darling habour precinct is good if you got good game
Any CBD pub where tourists hang out like the irish pubs, same goes for The rocks area, full of hard drinking tourist women and locals
Other good places are Surry Hills - Crown St, food and pubs , most of which are very good i.e The Clock Hotel and Whitehorse , lots of 7's + at the clock on a busy night.
Oxford St CBD - trashy women but easy lays at places like Q Bar, Kinsella's etc..etc..
Someone mentioned Kings Cross already so i wont cover it, i hate the place anyway for various reasons i wont go into but please watch each others backs if you do venture there.
Glebe Point Rd Glebe - Some very nice wine bars have sprung up there now and they rock for picking up or taking women to for a nice time. there is great food there as well.
Newtown - Main St - lots going on and lots of easy women at the pubs.
Bondi -quite a few good pubs there
Neutral Bay - The Oaks Hotel - very big, very busy , good food and decent women.
North Sydney - Fire House - Thursday and Fridays, Tree House same nights, Corner Bar, same nights....office women that tend to drink too much
As to where to stay I think the CBD, Pyrmont/Darling Harbor or Surry Hills is your best bet using cost + reward + logistics + facilities as the formula , or on the Harbour if you can swing the cost but expect to pay top dollar for a short term stay in a dope pad.
hope this helps and good luck with the trip