Oh, yeah, I should have mentioned that if you come up with a few domains you really like that are taken, you might as well contact the owner and see what happen

Oh, yeah, I should have mentioned that if you come up with a few domains you really like that are taken, you might as well contact the owner and see what happens. But if they want thousands of dollars that you aren't willing to part with just for a domain, looking for obscure ones is probably the way to go. Also, while it is true that domains are an investment, I'd keep in mind that they're pretty risky and illiquid investments. Unless you negotiate well or get someone who doesn't know the market value of the domain, you're probably going to pay approximately what you'll get for it if someone actually comes around wanting the domain. But that might not happen or might not happen for years. I guess there are probably domain squatting sites that would buy the domain from you, but probably for much less than what you paid, especially since you're approaching them, so they know you want to get rid of it and would probably do it for much less than what it's potentially worth.