One would hope that a city the size of Portland would employ a team (programmers & designers) to plan, design, & code the final design. There are many folks out there who can do both well and they are in high demand in the market place.
The worse sites I have ever seen are from programmers who write beautiful code and think that means they can also design or even place data or form fields in a logical or easy-for-the-user-to-follow manner - and - from the artist who who doesn't understand how to make a design that works on the web, or even if it can or should be done.
It is a misconception that you are either one or the other but examples of this are many.
Why is it that everyone has an opinion about what a good website design is? Remember to look at a site from multiple points of view...Why do companies have sites that you think suck? Because most likely they work: they get results; sell products; or present the intended information. Don't judge till you know.
But I will grant you this: Currently, the majority of clients I am talking to want a $12,000.00 site but only have $1,200.00 to spend. Something has to give and usually design suffers - or - you get that simple navigation script instead of that full, intuitive, nav system you need - or - a 4 page package when you really need 12, etc..
Great Idea= opening the design up to the public. New ideas and innovation may come as a result.
Take this article we are all responding to with several grains of salt: Who are these firms and designers who are "freaking out"? I like Tech Dirt a lot but sometimes there are little snippets that are short on fact & high on insulting opinion intended to get folks all worked up!