It sounds rather like you need a streetmap of each city, where you can
colour streets say red for "already chosen by someone else" and green
for "choose me if you like" ?  Or is it okay if user's choices have
common segments A-B-C-D , X-B-C-Y ?

I would suggest tile overlays as the best way to implement that
visually.  Users clicks could be sent back to your server to identify
the selected street and check if still available.

I would suggest abusing Google's directions service to obtain a full
set of city streets is not the best way, you might look at
OpenStreetMap for data sources.

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