It seems to me that milling a location followed by immediate paving would be much safer and less damaging to everyone's vehicles. Once that street is complete, move on to the next. This is typically how I've seen it done in other areas. If that's not feasible in New Haven, at least do a bit of patching after the milling so the transition between milled and non-milled surfaces is less jarring (and damaging). I'm sure many residents would appreciate this!

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