It's always a negotiation.
It's true: we must remember that infrastructure is highly impacted by the political and social climate in which it's developed. Would you lay out certain cities or transport schemes the same as they are if you could go back and start over? Doubtful. Balancing private negatives for public positives is, and always will be, an issue. (Take I-95, for example: it may be a great artery, but it cut off water access for a lot of cities and towns.)