The City of Milwaukee has recently announced that at it's current pace, the average street won't be repaved for more than a century:

At the rate Milwaukee city forces are working, the average neighborhood street won't be repaved or rebuilt for 163 years - more than a century longer than it's designed to last, according to a report released today.

Alleys will wait even longer for renovation - an average of 272 years, or about 200 years beyond the end of their useful lives, the report says.
...
As in the past, the comparison report found that total city taxes, user fees and city spending are all lower per capita in Milwaukee than in most similar cities.

Although Milwaukee ranks fourth in property taxes, at $377 per person, it comes in last in total taxes, because every other city studied also levies sales, income, vehicle or utility taxes, the report notes. For example, Cincinnati ranks sixth in property taxes, at $205 per person, but first in total taxes, at $1,327 per person.

Of course.  Must.  Raise.  Taxes.  However, if I may offer a more humble suggestion.  I imagine you could easily cut that replacement time in half (or even more), if instead of having every construction guy with a shovel be supervised by 3 other guys drinking coffee, every member of the construction crew actually got in there and worked.