Ok, each 'plot' on the map (note some of the buildings they have built cover more than 1 plot) is meant to support about 250 people. A quick google search suggests 250/acre is realistic for a medieval city, so we can use that as the basis, therefore each plot is about 1 acre, is about 200ft x 200ft. or in squares 40 x 40

The map I have for Olegs is 28 x 22 which makes it too small. On this basis, so I have my first decision, do I have various stalls set up against the outside wall of the old fort, or do I have it as a higher density plot?

After a bit of thought I like the idea of a walled in bazaar, and am happy with it building upwards to cover expansion, so I am going to leave it that size.

Ok, the smith district then goes around the main road into olegs, and gathers around that main route. The bigger houses can then back onto the wall itself or on a new path striking east (towards the first farmlands they settled).

Which gets us the city looking like this at phase 2

Click image for larger version.  Name: phase 2.jpg  Views: 86  Size: 39.5 KB  ID: 45592