1842/43 Citizen Roll for Brisbane Ward, City of Sydney has Robert Craigie rateable property - house, Sussex St.
1845/6 Roll of Electors, Electoral Roll for Sydney, Gipps Ward, shows Robert Craigie, dwelling house, Crescent St.
1848/9 and 1849/50 same as 1845/6 with Walter CRAIGIE listed at same address
1851/2 Roll of Electors, Electoral Roll for Sydney, Bourke Ward, shows Robert Craigie, dwelling house, Castlereagh St.
The index I have access to is supposed to cover to 1864 but there are no more entries for Robert or Walter after 1851/2. They are the only ones with that surname on this index. Women, of course, are not voters so can't tell if Janet was with him.
There are some entries on Sydney Sands and McDougall Directories up to 1876 but that's forty years after he arrived - could be a descendant. The Robert mentioned is living in Glebe and has 'fancy bazaar' next to his name - the mind boggles

Cheers, Judith