I consider it fairly unfortunate that about ten years ago i got into 'domaining' as I've never really found it to be profitable or very helpful. I've made a few thousand dollars buying and selling domains and sites, but not much more than that.
Part of it is that I got in a bit late and missed the boom times when you could buy 3 letter.coms, dictionary words, or even relevant pronounceable nonsense words like google or tumblr or flickr. :)
I did have a few I should have held onto but let go.
Terrorsuspect.com was a good one. As was RoughLiving.com which after all was the name of my first book and is still the name of this blog. Existensis.com was kind of cool and chrisdamitio.com was certainly one I should have kept but at the time $1000 was more necessary than a domain of a name that I don't use except on the most official of documents. More master plan to create a media empire around the word fukn didn't work too well and I sold off fuknbooks.com, fuknrecords.com, fukn.us and the rest of the fukn names for slightly more than I paid for them all in registration and renewals. I nearly got sued for JaypeeMorgan.com and SouthAmericanExpress.com and my attempts at cornering Moroccan traffic with alif-fez.com and theviewfromfez.com didn't work. No one really cares about those sites that much. There are literally hundreds more that I've bought and dropped, in some cases developing sites or blogs and in most cases selling them and letting someone else let them expire and drop. Even likelike.us didn't work but that's probably because facebook squelched my like script within days of launching it.
I've held onto clownjazeera.com, hawaiihikers.com, sunseaadventures.com, moroccoblogs.com, vagobond.com, vagobonding.com, vagobunny.com, usdebooks.com, nicehuman.com travelhotel.info, moroccosahara.com, thexboxaddict.com, searchcountry.net, emagdna.com and bloggermoneypro.com. Mostly because they all earn a little bit of cash and pay for themselves.
But I think it's time to let bekobe.com, bestmanalive.com, watch-lost-season-5.info, webbusinessexperts.info go the way of usdephones.com, translatorfree.info, seamonster.info, squealing.info, and easyfastdate.info - how in the world did I think those were a good idea to buy?
I'd like to get it down to ten domains so I will probably unload thexboxaddict.com , usdebooks.com, bloggermoneypro.com, emagdna.com, and searchcountry.net sometime before they come up for renewal.
Meanwhile, I'm moving towards using the free resources on the net since my sites are rather specific and no longer really hold for me to babble on about whatever I want or narciscistically like I'm doing here on this free blogger site.
As it stands now - Vagobond.com is about world travel
Vagobunny is a failed sexy woman site
Vagobonding is a failed social network
Usdebooks.com is nothing really
clownjazeera is funny
and the other five are just sitting.
Meanwhile, I'm babbling on here, at posterous, on mlkshk, and of course on Facebook, Google+, and Twitter.