Re: $$$
Just speed up the inevitable and feed the root servers a dictionary or ten*, then allow every word in any language as a TLD. What could possibly go(dot)wrong?
I love that (dot)wang is now available as a gTLD (fnarr, fnarr), and the rest of the list (http://en.wikipedia.org/wiki/List_of_Internet_top-level_domains#ICANN-era_generic_top-level_domains) has some other 'interesting' ones, apparently:
"The .ROCKS new generic top-level domain... is designed to channel the enthusiasm of millennial-generation youth. Individuals, bands, and youth-oriented businesses will all want to jump on board. .ROCKS is so widely applicable that it can truly be all things to all people. Geologists, of course, will be likely to register domains like igneous.ROCKS." (sic) (http://www.uniteddomains.com)
*I know it doesn't really work like that. Probably.