@ib2 @T-3D I've been a domain investor for over 10 years and have been very successful at it. There's a lot more that goes into it then just registering a domain name and hoping it will sell. You can list your domains on Godaddy auction listings or on premium listings, I've had a lot of success with those. Some good resources are namebio.com, dnjournal.com, namepros.com and others.
Once you decide to sell a domain name, it is important to find the best market to sell it. The best way to sell a domain name is to approach buyers secretly. If you know someone who deals with domain names, it is recommended to contact him without going through the middleman. Chances are that the seller will make more profit, as he will not have to pay the middleman.

Once you’ve settled on some domain name ideas, you can head over to a bulk domain search tool such as DynaDot’s to mass check all the names against different TLDs. When you’ve found one (or a few) good candidates, you can simply go ahead and register them for approximately $10 each. The next step would then be to market them. Then finally, it’s a waiting game.

I did this last month, snagged a great domain that no one else found and got it for $69 because I waited until the last moment to place my pre-bid. Flipped it within a week for a little over $1,000. And probably could have gotten more if I sat back and waited 6-12 months, but a bird in the hand… (plus I like to keep turning over inventory and maintaining cash flow).
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.
There are many places and ways you can purchase domain names.  You can purchase unregistered ones through sites like GoDaddy.  There are forums where people will gladly try to sell you their domain name (usually though the domains being sold in forums are either crap or the asking price is so high it does not allow you any room to flip the domain).  And then there is my favorite way of obtaining domain names, through an online auction at Namejet.  Let’s first talk about Namejet and then we’ll talk about how I personally ring the register by flipping domains.
When a domain name that was previously registered expires, it goes through a grace period that allows the previous registrant one last chance to reclaim their domain before it becomes available to new buyers. If the previous registrant still has not renewed their domain after the 77 day deletion process, the domain name will officially expire and enter the Aftermarket.
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.

Your course of action really depends on how much work and effort you can put into the expired domain. If you're barely able to maintain and optimize your current site, you probably want to just 301 redirect the old site (note: see my amended comment above about the link value not likely to be passed). If, however, you're more creative and have some time on your hands, you can try your hand at crafting a microsite. If you really know your stuff and are experienced at making money off various websites, you'd probably do well with the third option.
In theory, you could technically acquire a domain for $10,000 and be able to sell it for $100,000. You could also acquire a domain for $10 and be able to sell it for $100,000, $10,000… or $100, you get the picture. Because of this, it’s hard to recommend a perfect starting budget because your strategy, experience, and the pace at which you learn will hugely affect your buying and selling decisions.
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