I think the cruise ship thing is a horrible idea. It seems like a libertarian town, or gated community is pretty much the only answer.
There already is a condo cruise ship.
Cost of entry keeps the riffraff off.
http://www.cruisecritic.com/reviews/cruiseline.cfm?CruiseLineID=210
130 families hail from 19 countries throughout North America, Europe, Asia, Australia, South America and South Africa. Some live on the ship year-round, although most tend to be onboard for three to four months. The ship has an average occupancy of 150 people. Potential buyers must have a minimum net worth of $10 million to buy from World of ResidenSea.
There is a guy in Maine, Allen Weiner, who did the offshore radio pirate thing and got busted a couple of times, now he runs a licensed station.
Weiner and Ferraro continued throughout the 1970s and '80s with various unlicensed stations. Some projects were operated separately from one another, but others saw the duo collaborating as they did on Radio Newyork International, which operated from a ship, the M/V Sarah in international waters off the Long Island coast. Again raided by the FCC, Weiner and Ferraro began purchasing airtime occasionally on licensed shortwave station WWCR.
Another attempted shortwave station operated from a ship at sea, this time from aboard the M/V Fury and operated from off the South Carolina coast, was raided before the ship had left the harbor when the FCC claimed to have monitored test transmissions coming from the ship. The South Carolina operations were to be funded partially by controversial fundamentalist preacher Brother Stair, whose broadcasts would also be carried from the ship. The ties to Stair, whose views stood in sharp contrast to Weiner’s, led to accusations that Weiner had “sold out” his long-held beliefs in religious tolerance and eclecticism. Stair frequently clashed with Weiner and especially Weiner’s engineer Scott Becker during the abortive project.
After the M/V Fury fiasco, Ferraro purchased a small licensed AM station, WHVW in Hyde Park, New York.
In 1998, after a decade of lobbying and another threatened off shore broadcasting effort, Weiner was granted a license for shortwave station WBCQ and AM station WREM in Monticello, Maine.
Programming on WBCQ is an eclectic mix of music, plus brokered religious and political programming. Some former radio pirates produce shows on WBCQ as well. WREM is now known as WXME, simulcasting WSKW Skowhegan, Maine, an oldies formatted station previous formats on WXME include news/talk, simulcasting Caribou-based music Channel X Radio under the call letters WCXH and as WREM rebroadcast the talk programming of Presque Isle’s WEGP. Having received a license after years of battling the FCC has brought more criticism from pirate radio enthusiasts. Also criticized has been Weiner’s sale of airtime on WBCQ to the incendiary government informant Hal Turner and radio preacher Brother Stair.
WBCQ’s first service operated on 7415 kHz, a frequency that was the most popular for shortwave pirates in the early to mid-1990s.