It’s something I’ve been trying to improve for years now, stripping emotional attachment out of the equation and focusing on ROI when it comes to domain pricing. Since I started in the domain name world I’ve tried to sell domains for at least 10x what I paid for them. Compare this to any other industry on the planet and those would be ridiculous expectations but as we all know, domains are different.
Here’s the challenge I always run into. There are plenty of domains I paid $100 – $200 for that I get inbounds on but quote at $2,500 – $7,500 based on the name. Every time I do this I think to myself, “am I just preventing a sale and a 10x ROI because I feel like I could get a better price for a domain?”
Since I’ve sold my fair share of domains for 20x or more ROI I do know it’s very possible, especially when you’re looking at domains that you bought for a few hundred dollars. Hand regs are the hardest for me since I’m not interested in selling a domain for $100 – $200, and I’ve sold hand regs for $5,000 in the past so I know what’s possible.
The question I always ask myself is, should I focus on making sure I hit a specific ROI goal or should I keep going down the path of evaluating the price of each name and trying to get what I think is fair market value for each?
How do you price your domains? Comment and let your voice be heard!

Long version: my experience and POV slants towards each domain being unique, understanding that markets and circumstances change / evolve / deteriorate (so stay current on the subject matter of your domains) AND, lastly, history of reported past sales informs / guides but is not determinative. (I read DNJ’s weekly reports and a few other reports, ever mindful that almost all of me personal sales are unreported and, I suspect, so are the sales of many other “Domain Goldrush” era (late 1990s) domainers. Frank S’s recent domain sale data dump may also be helpful, but the scale and changing of his operations has to be taken into consideration.
Short version: it all depends.
Most of what I acquired over the years I acquired with a minds to eventual development, but life usually intervens. Sometimes I may choose to accept an offer, abandoning the idea of developing a “unique address”, simply because I’m busy on other projects OR the influx of cash might be used to support a project in development.
So, to directly answer your question, IF you have the time and IF the value of that time will be reflected in the ultimate outcome – a sale – then evaluate each domain on its own merit. However, if you are dealing in individual sales of domains for hundreds, not thousands, of dollars (I doubt you are) then, unless you are living in an emerging market, chances are that the brain cycles will be better applied to more profitable endeavors.
Pleasure talking . . err . . monologuing . . as always, Linton.
Regards,
Jeff / a/k/a CrankyOldMan at DomainState (R.I.P.) and still Webwork @ WebmasterWorld Domain Forum (cranky old moderator).