When I first started online, I'd register domains that I thought I could develop and sell at a later time. After learning my way around the cloud, I realized many of the domains I'd registered are pretty much useless, or so I thought, and I let them expire. Come to find out several of these domains have been picked up by parking sites and are being offered for sale for thousands of dollars! Now I'm not saying they're actually selling for the asking price, but I learned my lesson. I never allow a domain name to expire. I add content to it, backlinks, some AdSense and try to sell it for something.
Think about things like contractor.com or oranges.com. The more generic you go, the better off you will be. Why? Research has shown that Google likes generic names, so any company selling oranges may, for example, want the oranges.com domain name. If you own that name, you can set the asking price for it. Sounds great, right? There arejust a few things you have to think about first.
Contains, Starts, Ends You can use the search bar to search for domains that contain particular keywords you are seeking, e.g. a search for "car" will yield results for all expired domain names that contain the term "car". You can also use the search tool to find domains that begin, or end with the search term too, with the drop down box next to the search form.

Most domains traders, or resellers, buy hundreds of domain names. This way, the chances of hitting the jackpot are higher. But, this takes some up front money. You can start with a handful of names and work your way up. This is the best way to begin. You may also decide to purchase a name from another seller if you think that a name will be big enough.

Here's an old post on search engine roundtable that claims google's policy is to discount previous backlink juice when a domain changes ownership.  I'm not convinced whether this is actually true or something Google says to discourage excessive domain buying / 301 redirecting for SEO benefit.  The comments above seem to give varying opinions on this matter. Would be great to get to the bottom of that one!
I don’t think that there is a real way to sell your domain fast, you can put it up for sale, depending on domain name, but if there is a fastest way to sell domain name, it’s certainly - having a good enough name, that someone would want to buy. I don’t like .com domain names, but that’s my opinion, instead I prefer Hacks ( I’m from Serbia, therefore most of word in English, in plural ends up with ‘s’, so every word that ends with letter ‘r’ in plural gives you .RS ) so I think that here we have great Hack domain names which would sell fast. Either way, your contact information should be available in WHOIS , so if you have an interesting domain name, every buyer would like to be able to contact you directly.
There is a misconception that good ‘.COM’ domain names are hard to find and so they are more expensive to buy. But once again, this statement holds no water. You can easily check out the ‘.COM’ domain names that are on sale at highly affordable prices. However, the only downside to flipping ‘.COM’ domain names is that you will have to discover them at different places like Flippa.com or private seller portfolios.
Once you get to this point you know there have been DMAS listed. They have a number of domains linking to them and according to the way back machine which is WBY, you can see their site age. So, if you want to go with an older site you can see right here whether or not this is a site that you might be interested in, but before pulling the trigger you do want to check two things.
Hey, what’s up everybody. It’s Brian Dean from Quick Sprout. In this video, I’m going to show you how to buy affordable expired domains and how to evaluate the potential value that an expired domain could bring to your site. Now, expired domains is pretty gray hat, black hat type of thing because there’s basically two things you’re going to do in an expired domain.
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”.