These should be more than enough to get your domain in front of tons of potential buyers. If you did a good job picking an awesome domain, you should have no problem (eventually) selling it. You need to be very patient as it could take months or even more to land a decent deal. A lot of domainers sit on domains for years before actually selling them. This is why it’s best not to obsess over a domain and simply move on with buying and listing others (or going back to your day job if this is a side gig) once you've listed the initial one.
It’s also not so easy to manually re-register. This is due to backorder providers which are paid to keep an eye on expiring domains over a certain period of time and then register them for the customer as soon as they become available. Promising expired domains are therefore usually sold before they have a chance to be put back on the registry menu for the public to look through.
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.

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!
It's ranking high today! What could be the problem? NO. JUST STOP. Unless you know the entire history of a domain, you may be setting yourself up for failure before you begin. SEOs (and business owners) use a variety of tactics to get a site ranking high in search results. For some of these methods, we'll just call them "questionable". These methods could include everything from buying links, overuse of directory submissions (non-industry related), duplicate listings, poor quality backlinks, and guest blog comments.

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.
Length: This is pretty self-explanatory. Generally the shorter the domain name, the more valuable it is. This difference in value decreases exponentially as the name gets longer, though. For instance, the difference in price between 3 and 4 letter domains are significant, while the price difference between a 7 and 8 letter domain would usually be much less significant.
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