One thing to keep in mind for any city website is that it is the online face of the city, and may draw an audience demographic composed of a much larger population of novice or inexperienced users than other types of sites.
Beyond the existing suggestions of making the site's front page as simple as possible, the overall design of the site should be assistive whenever possible. Most novice users find even their own computer equipment somewhat intimidating, and find most websites (even ones well designed for more experienced users) far more so. The current website design is almost a textbook case of how to scare off a novice user, with an almost two page long navigation bar at the left full of cryptically abbreviated options, and a random uncategorized selection of news articles and calendar entries, all in medium to fine type. The Help link, a tiny anchor on the very top toolbar, opens another 2-3 pages of text in fine type with links scattered through it -- most novice users give up at this point and drive to City Hall.
We could do *so* much better.
If nothing else, make the initial page simple and friendly, with clearly labelled options that cover maybe 3-4 broad categories of city services at most, and for novice users, include an option (such as "I need to..." or "Help me...") that opens a fully-assistive navigation wizard, which uses expert system methods to determine what the user wants to do and guide them to short lists of clearly worded links to key pages in the desired category.
Add user assistive messaging as well, possibly triggered by unusual click patterns (caused by randomly stumbling around because the desired content isn't coming up as expected), that either feed into the expert system or provide tips based on the click trail, or both ("You seem to be looking for X, do these links help?"). The messaging could automatically turn off as the user gains experience with the site and, ultimately, is no longer a novice.
We don't have to teach users how to browse web pages, but we can definitely provide a good model within which they can teach themselves to use this one, and maybe carry a few good habits away with them.