The first problem is that no one at City Hall seems to ever ask the question "what's the problem?" The City's inability to ask, and answer, that question prevents them from providing a cogent description of issues being addressed, potential solutions and the criteria for evaluating options. Simply because the fundamental problem is never clearly stated.
We've recently seen this with the Pavement SNAFUs. What was the real problem being solved by the high school roundabout? Were the intersecting streets thoroughfares or were they intended to become through-ways? If so, this should have been clearly stated upfront in the problem statement. Then prioritizing the importance of pedestrian traffic would be clear. Perhaps City Hall was afraid of being honest with the citizens by stating the dominance of business related traffic over residential traffic and related concerns.
A similar situation occurs with the IT efforts. They have only a hammer and consequently only see nails. Since they're always going to use the same hammer it is simply a waste of time to ask "what's the problem?" since they only see one solution. It's as if they believe the "I" in "IT" stands for "idiot". By refusing to clearly articulate the problem at hand they have been unable to prioritize concerns and make intelligent, informed technology decisions. And they waste quite a bit of our tax dollars fielding inadequate "solutions".
Until this City starts with a clear problem statement based on sound analysis that establishes clear goals any attempt to move forward will be met with resistance and every issue will become a wedge issue.