The second option requires a bit more time and effort than a 301 redirect. You could do a mini overhaul of the site and turn it into a microsite for your main domain. This option is good for exact-match domains for your targeted keyword, and there are other reasons for going the microsite route that Rand's highlighted in his post about root domains, subdomains, subfolders and microsites. This strategy also works better if the old domain has decent rankings for the keywords you're targeting.
Also, I currently have two other domains that are registered with Squarespace, and I have their annual payments set up automatically so I never have to manually pay (and so nobody else gets that window of opportunity to take the domain away from me). Would it be possible that the owner of this domain might just have a similar system in place and that I might be wasting my time?

There is no easy way to explain “all” things about expired domain names. As you stated Michael, Network Solutions domain names go to the partnered domain auction service NameJet.com BUT, not “all” do… NSI customers have the option to opt-out of having expired domains go to auction. If a customer picks this option, the domain name would go through the drop process and go PendingDelete around the 71st day after the expire date. When it is released from the registry, the domain name is fair game to the major dropcatching services and the private ones. This still doesn’t mean anybody would grab it, and the domain may become available to hand register.
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.
Answer: Many auction sites will allow you to backorder the domain name for free. Follow the process above to find the domain name registrar and auction partner site. Then sign up for an account at the auction partner site and enter a backorder. But remember, the domain name may transfer to another registrar at some point so refer to Step 1 above periodically.

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.

Since high quality expired domains are in low supply, the huge numbers of marketers competing for those drop domains tend to drive prices up. Also, if you use an exchange, you’re basically lucky to get whatever you can afford. In other words, niche specificity isn't guaranteed. This is going to be a problem because as Google continues to evolve, it is cracking down on domain niche relevance. In other words, its software is fast evolving to the point that it can tell what the niche of a particular domain is. If your private blog network is a patchwork of expired domains that involve many different and dissimilar niches, then you might be in trouble. You are at great risk of being penalized by Google.
DomCop has a great offer that all of you buying expired domains should consider. For the price of a couple domain names, you can use DomCop for a month, snag some excellent domain names, which would otherwise cost you thousands of dollars. If you're considering expired domain software and don't have the knowledge to program your own crawler, I'd lean towards DomCop.
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.
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The whitelist filter for wanted characters is now split into three filters. The old whitelist is now named whitelist (only). When used, the domain has to consist only of the defined characters or numbers. No other characters are allowed. The new whitelist (any) filter finds domains that have at least one of the defined characters or numbers. The new whitelist (all) filter finds domains that have all defined characters or numbers at least once.
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