It is much harder to sell names no one has heard of. Short names have the highest value — they are rare, easy to sell and bring substantial profit. Basic and common domain names, which can be relatable, or arouse interest in the market are the best. General names sell thick and fast and also bring considerably higher profit.  Names that are easy to spell will attract buyers, and provide good opportunity to make a decent profit. If you know you have a good domain in your hands, then you are likely to make good profit by selling it.
Expired domains are domains that have been registered by individuals, businesses, or organizations, but aren’t renewed after the contract ends, or are deliberately terminated. That means that they available for re-registration. There are many reasons why someone would choose to abandon a domain; one reason could be that the web project failed, or that a domain portfolio went into liquidization. Domains can also end up becoming free due to the owner receiving warnings for possible trademark infringement. Re-registering can also result in legal consequences.
Yes, we port in all of the domains from NameJet, SnapNames, etc. There are a lot of great deals to be found. Some are absolute trash of course but if you can sift through them and put some time in (hopefully that is what we are trying to do with our tools is save time and give some value add with the SEO metrics, alerts, etc.) then you can find some great bargains.
What about option #4 - Redirect your existing domain to the old domain? I bought an old domain that is 100% relevant to my current domain but currently has with very little content. It did have more content fours years ago. The old domain is 13 years old, pr=3, while my current is 7 months old pr=1 and a decent amount of content. The old domain I purchased was not expired though and I do not know if this makes a difference. What are the pros and cons of option #4? Am I correct to think that option #1 would result in no benefit from the old domain's age value and if so why is it not listed as a con, a MAJOR one. Its hard to believe that a 301 using option 1 would give my existing domain 13 years credit but I'll take it if it does.
Domain name expert Bill Sweetman has provided strategic domain name advice to major companies around the world for over 20 years. Bill is the President & Lead Ninja of Name Ninja, a boutique domain name consulting firm that helps companies acquire, manage, protect, and profit from their domain names. A self-confessed domain name fanatic, Bill registered his very first domain in 1994 (which he later sold for five figures) and has been perfecting his “Domain Karate” moves ever since.
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I OWNED DOMPERIGNON.ORG, incredible, but true.  Lost it, back in the days when internet in India was not a readily accessible utility. And I was a casual domainer.  You had to go to a cybercafe. Did that late in the day, towards the expiry of the domain. No chance of renewal. The domain is now with the owners of Dom Perignon and is redirected to domperignon.com! 
I have an interesting twist on how I have done it in the past. I will buy a domain and use it as a development domain for blog posts and things of that nature. Then over time it will gain DA and PR. Then I will sell it off and buy another development domain and start the process over. Not quite the process you mentioned, but it works. People will link to the development site to show things off as well  sometimes, so that helps.

Sellers should also learn to identify premium domain names. Dictionary names are premium domain names. Domain names with dictionary-singular names are the hottest on the Web, and buyers are willing to pay a lot to purchase them. Names, such as search.com or askme.com, will get buyers more easily than long domain names. It is also important to note that unhyphenated domain names have more value. Even product-related domain names also can enable sellers to earn substantial profit. Once a seller has a certain degree of knowledge about the domain, he can start searching for buyers.
The domain name industry is quite similar to the real estate industry in a lot of aspects. There are end users, brokers, consultants and domain flippers or “domainers”. Domain flipping works similarly to buying a house, renovating it (or even sometimes just sitting on it) and then selling it again at a higher price point. The gist of it is: you’re purchasing a domain name and betting it’s worth (or will be worth) more than you paid for it. If you’re right, you get a nice paycheck and move on. Those who make a living out of this just rinse, repeat, and scale.
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