Having been around the Micro Movement for years and years. I am going to 'repost' a recent letter to some of the folks from the now off-the-air Liberty 1640 during some recent correspondence. That station was being harassed over the ground conductor length of a measly 100mW Part 15 station.
Anyway this is an idea I have had floating around for quite some time.
You want to know what I think would work well, especially in larger cities?
An 802.11 WIFI style station.
Picture this, a MAX power Router or array including extended Routers or Access Points. I would need to double check but I think you are allowed upto 1 watt.
Then have NO gateway to the Internet and no connectivity to your personal machines.
Have the DNS given out at DHCP resolve ALL addresses to a single Server for YOUR Web-Page where you have YOUR favorite video Documentaries and Exposés hosted. You could also stream live local shows.
The benefits are cheap price, More exposure to younger folks than AM radio, no need for people to run a channel scan for TV. Also as of yet I have heard of NO FCC busts of WIFI stations even for excessive power.
Also by watching the MAC addresses you can get an idea of how many people are connecting to your server. That is cool because you could start very small with a router in your attic and test the concept.
Imagine, you would just always be there in the WIFI lists on Laptops, PCs and many new multi-media portable devices.
You could also "re-stream" radio shows or re-stream the entire radio networks like Oracle, RBN, Liberty News Radio or even GCN- When Alex isn't on...lol
Drawback?
The only thing I can think of is that people "may" be able to exploit the system to interconnect their gaming machines or transfer explicit files but I doubt anymore than they do with open hot-spots and networks already . I really doubt that would be a problem but you could always attach a linux firewall for cheap.
Think about it. A few well placed WIFI Router Antennas that would cover a city for not much more than a couple Rangemasters. If you know a decent webmaster to help you with a cool multimedia page to serve up the videos and audio streams to the public, you have it made.
Anyway I have had that Idea for a while but since I am so rural I have never pursued it. However I do see WIFI networks from over 3 miles away at my house and I'll bet those routers are sitting on someone's desk in their office

Just think when you put the router in your attic with about 20 feet of LMR-400 to a hygain antenna 15 feet above your roof (2-way linear amp optional) hehe.