Thanks for the input. I checked out the Joomla website and really like what I see. Is it hard to develop your own site? Hard enough to hire someone else? I realize the cost of obtaining a city.com, but feel that overtime, a high quality site would bring in more ad revenues.
Yes you can definitely develop on your own and that is what I generally do, but you will need to invest a lot of time, and the quality will probably be far lower. The point is, is that if your already investing large sums of money for the domain, why not go all the way with a top notch site, which will be ready right away. The content of the web-sites are far more important than the domains, look at Google and Yahoo. You should start learning how to use Joomla anyways, since you will be constantly adding content and developing.
I agree that in the long run a high quality site will pay off as you stated, especially since once you have your site up, advertising will be a much smarter investment, since you have good reason for your users to come back.
You should look at $x,xxx app. for small towns,
$xx,xxx big cites,
and $xxx,xxx-$x,xxx,xxx for very big cities,
therefore your web-site development which is the most important, is a small investment relitively.
Wordpress is very good, but very limited, meant specifically for blogs, with some nice add ons. If your looking for building a major site, with lots of power, my suggestion is Joomla.