Really depends on whether you want it to be passively marketed or actively pitched to investors and buyers, as well as how fast you want it sold. It also depends on what you're selling. What you're selling is only worth ANYTHING if there is an interested buyer. And it's only worth what the buyer is willing to pay for it at the time you want to sell it, not what you currently owe on your RV. This is a common misperception among folks trying to value domains before sale - they pick some nebulous method of pricing it that is not based on the market or history or sector demand, but rather on what a vacation costs or how much they owe on their boat. Good luck with that. So it really depends. If you have something that you feel has demand, you'll potentially get a higher price for it by NOT needing to short sell it quickly for cash and being able to wait while a broker packages and pitches it. 60-90 days. That will always get a higher price than just listing it in a database and hoping someone will see it and be interested. The problem is, good brokers are few and you're going to need to see if they will represent you in the sale. If they don't believe they can sell it at all, or they don't believe they can sell it for what you owe on your boat, they'll decline your offer to do business with you because you're being unrealistic.
One big tip is to find a domain that someone can make money with. If you only owned that 1 domain, could you earn a living? This helps you focus on the top 1% of domains and ignore the junk that you will struggle to resell. You must get this right because domaining can bankrupt you fast if you buy the wrong domains. Godaddy is also great for grabbing expiring domains for much less.
Surely if you purchase a domain (domain1.com) and redirect it to your existing domain (domain2.com) you expect to loose all ranking for domain1.com. If 301's are used then the objective is simply to pass on authority, not dominate the search results with 2 domains. If you want to keep domain2.com in the index then you would take Rebecca's option 2 or 3.
However, I'd argue that most people in the business really struggle as they don't understand what makes a good domain name and what's a bad domain name. While I do not work in this field full-time, I can say that I can make a living of it, but it's probably because I don't ask for absurd prices (e.g. randomword247.com domain name for $8000 is just unrealistic and won't happen) and therefore can sell domains easier. 
Your system is broken, You took my lising money on an open domain http://www.australianfintech.com.au and then stuffed me around something cronic and no response from your supoport team either. I have spoken to Tony who is one of the main people there at a function and I will move heaven and earth to find his number and give him a piece of my mind!! I have 60+ domains to sell but it seems you do not want the business! BAD MOVE not accomodating clients!
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”.
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