Hundreds of thousands of domains expire everyday. While most of them are trash, quite a few are aged domains having excellent backlinks. These can be easily filtered using metrics from Majestic (Trust Flow) & Moz (Domain Authority). These are great for your money sites or for building private blog networks. Some of these domains have natural organic traffic, that can be determined by their SEMrush rank or the SimilarWeb data. These are great for domain parking or for promoting affiliate offers.
If you buy keyword specific domains, you're really buying the type in traffic. I use the URL builder and redirect through that URL so you can see how much traffic your getting from the keyword domain. There seems to be no rythme or reason to what keyword domains deliver traffic and what don't. By tracking traffic with the Google URL builder you get a feel for what names are giving you traffic and which are not. ie. the plural, the singular, two words, three words, the possessive, etc.
A domain name that reaches expired status and is not renewed by the owner will be listed at an auction service (see FAQ for exception to this rule). The domain name does not immediately go into auction, but is immediately listed on the partnered auction service with an auction scheduled for the near future. Such a domain name will be exclusive to that specific auction service.
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There is a common misconception that domains expire on their expiration date. If a domain registration is not renewed by its expiration date, the domain simply goes into "expired" status, which means all services are shut off. Typically, we provide a 35-day grace period during which the current holder can still renew it for the standard renewal fee. For more information please review our domain deletion policy.
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?