Re: Looking for some domain name advice
You can also ask him for traffic statistics to justify the price he's asking for the domain. However, if it's not generating enough traffic to keep the owner's interest, you can argue that the domain is essentially worth very little at this point, or he would be keeping it. Then, of course, the domain will be worth more once you drive traffic to it.
Regarding the extensions, I also agree that you shouldn't settle for another extension. I do sometimes register .net domains, but generally only when I also have the corresponding .com. I register the .net just to keep competitors from getting it, but I stop there. It would be cost-prohibitive to register all the other possibilities.