I've been on both the buy and sell side of this negotiation quite a few times. thistleco's advice is pretty good. I'll just add one thing about the new GTLD pro

I've been on both the buy and sell side of this negotiation quite a few times. thistleco's advice is pretty good. I'll just add one thing about the new GTLD program. Unlike the past, nowadays you are competing against the registrars themselves and the automated and MANUAL analytics they run on availability searches, whois queries and etc. As the OP said in a comment here, if you find a brand you like, don't hesitate because that name might be repriced by the GTLD operator due to your searches and activity around the domain.