Selling, for me, would be similar pruning a tree. Sometimes it's wise to remove some of the sickly branches to expose newer ones to the sun.
My friend (IceToEskimos) made a good point that when you sell a site, you're basically short selling it. That is, say you sell a site for $300. You're betting on that it will make less than that in the future, and the person buying is betting that they can take it and make it make more than that.
I agree. I've sold a few sites that were making $x,xxx/mo for low $xx,xxx to throw the cash into projects I cared more about.
I typically keep my eye on those sites after the sale, though. Most of the time the new owners run them into the ground.
Once...and just once...the new owner took the site and ran with it. It's now making between $10k and $15k per month basically on autopilot (its a membership site). Considering he paid me $18k for it a couple of years ago, I'd say he's doing pretty well.
If I were an asshole, I could throw up another site like it in a week and dominate that market again. But...eh. I have morals and he's a nice guy.
That being said I don't sell much. I like to get them to where they're doing their thing with little-to-no maintenance and enjoy the fruits of my loins...er...labor.
I sold about $100k in sites within a 6 mo range prior to penguin, all sites are off the map... I feel extremely bad for the guy, but maybe I lucked out?
There are some people who can profit from selling their online business or website. What would cause you to consider this, and have you ever done it before due to a life circumstance, etc.?
For example, $100 of today's money invested for one year and earning 5% interest will be worth $105 after one year. Therefore, $100 paid now or $105 paid exactly one year from now both have the same value to the recipient who assumes 5% interest; using time value of money terminology, $100 invested for one year at 5% interest has a future value of $105.