A good source of finding who lived at what address in the early years are the publications of Stones Directories. Not only did they give the name of the occupant/s but also their profession in most cases.
On 1st November 1912 Roslyn Borough amalgamated with Dunedin City, and at that time Kaikorai was part of the Roslyn Borough. The vast majority of Kaikorai street names were changed shortly after this, no doubt to avoid confusion with existing streets within the city. A 1913 Dunedin street map shows that most changes had been made by that time.
See also other Kaikorai/Roslyn maps, in particular the 1902 Street Map which shows the early names.
Check HERE for a listing of streets that have been scanned and what years they are.

Select street directory extracts from the year options below.
1888       1902       1909       1919       1936       1942       1950       1951

NOTES on shops in the Kaikorai area in vicinity of Jellicoe Crescent in 1936-1950

I have taken information from the following "Stones" Directories, 1936, 1942 and 1950.

Street numbering will confuse the issue if reference is made to more recent maps, but on the plus side the intersections are shown in the Stones Directories which gives a reference point.

NAIRN ST: Left side from Taieri Road. Currently No.15 is on the corner of Taieri Road (this used to be 33 in 1936) and 27 is at the junction of Jellicoe Crescent (which was 39).

TAIERI ROAD: It is interesting to note that in 1936 No.1 Taieri Road was at the intersection of Highgate where Laurensons Bakery driveway used to be, just down from where our Aunties, Grace and Win Bartlett used to live, and opposite the Roslyn Fire Station.

Number 1 was the fruiterer, Henry Marsden (1936 and thru to 1950 at least), then Bill and Reg Thomas's parents had it when I had started work, post 1950.
The others moving down hill from there are listed of course, going round the corner into Taieri Road as we know it today.

When we get to the intersection of Taieri Road and Kaikorai Valley Road we see that KFC (later Roosters Restaurant of Roslyn) is currently No.99 Taieri Road, and the house immediately up the hill from the Presbyterian Church is still 131 as it was in 1936 - so no changes there to confuse.

It appears that Taieri Road now starts at Kaikorai Valley Road and the section above that is now a continuation of Stuart Street Extension. See Roslyn Street names & numbers and view comparisons between 1950 and 2002 in the Highgate shopping area.

KAIKORAI VALLEY ROAD: Lefthand side from Taieri Road - 17 Kaikorai Valley Road is still at the intersection of Hereford Street as it was in 1936 - no change.

Righthand side from Taieri Road - basically all previous premises are gone - no buildings fronting Kaikorai Valley Road between Taieri Road and Mellor Street (which was not there till after 1950). Before Mellor Street was constructed first intersection was Greenock Street.

HIGHGATE: Righthand side
I've only included the section from City Road to the Tram Line crossing (now Stuart Street Extension where the overhead bridge is).   See more on this under City Road in Roslyn Shops Map

In 1936 the street numbers in this area range from 84 (Willie Wing - fruiterer) to 98 just before the tram line.

In 1942 the street numbers in this area range from 300 (Willie Wing - fruiterer) to 322 just before the tram line, likewise in 1950 except Willie Wing has been replaced by George Qu Wong at 300 Highgate.

CITY ROAD: Righthand side from Sligo Terrace
Things are pretty straight forward till we meet up with the Highgate intersection.
Listings in 1950 show that at this point City Road actually continued round past the Fire Station and encompassed the Self-Help shop, a draper, Roslyn Fish Shop and Roslyn Book Club (with a Branch Office for a coal merchant). These buildings would have been numbered 36-44 City Road, which incidentally used to be the beginning of Taieri Road.

City Road and that section of Highgate mentioned above appear to have been renumbered since 1950. The shops past the Fire Station appear to now be numbered 288-290-292-294 (which now coincides with Highgate numbers) and after the shops there's the track that leads down to Strathmore Crescent (previously Littlebourne Crescent).

See - list of changes to City Road and Taieri Road over the years.

See also maps some of which are showing shop locations.