I think a lot of cases are cut and dry - if a webmaster is going to register a doamain name that is similar to a long standing site - webmaster could be asking for trouble, for sure. Why give yourself a load a legal hassle on top of everything else I would say.
I see more and more domains that are a play on sponsor's sites names too these days - that's another gray area for sure, but I think a lot of sponsors must be turning a blind eye to that as long as the webmaster is using the domain to promo just their particular site - and what redress a sponsor may have legally to say someone registering chickswillgobothways.com 5 mins after sponsor launches chicksgobothways.com - who knows, maybe a precident will be set someday soon. And we will see webmaster of hornyblowjobslutsuckingcock.com sueing webmaster who owns horny-blowjob-slut-sucking-cock.com - and webmaster of hornyblowjobslutssuckingcock.com sueing them both..
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