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For the following TLDs you can now find a expired/deleted domain list. .gi, .gl, .gy, .hn, .ht, .ky, .mu, .om, .pf, .qa, .rw, .sb, .sm, .sn, .st, .sx, .tc, .tl, .ug, .uy They also show up in the Deleted Domains (last 7 days) list and in the Domain Name Search, however they are not in the pending delete list! I do not have a working droplist for them yet, so that is why they are not released in the pending delete list yet.
While numbers like those above are impressive, most domains sell for significantly less extravagant prices and are generally in the two or three-digit range. Not long ago, those who were able to secure general terms (like icecream.com or pizza.com) not protected by trademark rights often found themselves sitting on virtual gold mines. The glory days of this boom have long since passed, and those looking for a profit in today’s market needto have a keen sense for coming trends.
The second option requires a bit more time and effort than a 301 redirect. You could do a mini overhaul of the site and turn it into a microsite for your main domain. This option is good for exact-match domains for your targeted keyword, and there are other reasons for going the microsite route that Rand's highlighted in his post about root domains, subdomains, subfolders and microsites. This strategy also works better if the old domain has decent rankings for the keywords you're targeting.
So how do you develop that instinct? NameBio maintains a database of over 500,000 historical domain sales (as of writing this post). They have interesting filtering features by which you can narrow down domains by price range, date sold, keywords and more. Simply sifting through the listings on NameBio long enough will quickly develop your domain appraisal “instinct”.