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Answering this question is a big part of a planner's job, but to the premise of the question, the answer depends on whether you see the additional density or urbanization as a punishment or a reward. The real world answer will also heavily depend on context, like where the major job centres or transportation links are.

In the absence of this context and speaking in general, my own view is that the older semi-urban suburb will generally be the better one to urbanize, but not because it's likely to be closer to the centre city - it's because its better bones make it more receptive (in a technical sense) to density. The importance of the street pattern can't be overstated, and even a semi-grid network will be far easier to add density to and incorporate additional connections if necessary. On a dendritic curvilinear network in the suburbs, you get far more odd-shaped lots that have a hard time hosting much more than house-type forms (especially under our North American building codes) and street networks with offset street rights-of-way and property lines where connections are harder and less efficient to make. In a street network like this, even with a very high density that could theoretically justify great transit service and a great density of uses that allows for shorter trips, the circuitous routing between most two points means vehicles would remain favoured.

The point about the existing commercial setup is important too: even a strip mall-based main street is likely to be more tied into the existing street network and redevelopable over time. In the power centres serving newer suburbs, not only are they much bigger and more entrenched and therefore difficult to redevelop, but they're often found at the intersection of highways/arterials that isolate them from the rest of the community and which are very hard to retrofit, if even desirable.

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