We are a LauncHUB funded Startup that focuses on big data research of domain names and Whois information. SEO experts can use our unique system for finding expired domains with authority and backlinks. Investigators can use the same database to find information for domain owners and hosts with Reverse Whois and Reverse IP tools. We can also offer brands trademark monitoring in the vast pool of ccTLD domain names.

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?

Contains, Starts, Ends You can use the search bar to search for domains that contain particular keywords you are seeking, e.g. a search for "car" will yield results for all expired domain names that contain the term "car". You can also use the search tool to find domains that begin, or end with the search term too, with the drop down box next to the search form.
So, what I like to do is also choose DMAS listed entry. No fake or no unsure page rank. Click the apply filter button and this will show us a much better group of websites, including a lot of high page rank websites. That’s one great thing about Go Daddy Auctions that you don’t have to guess about what the rank will be which is not the case with a lot of deleted domains which, because they were deindexed they didn’t have any content, they didn’t have any hosting, they don’t have any page rank. So, you have to make an estimation.
We do not only have Expired Domains, but you can also find lists of Deleted Domains for a lot of TLDs. Deleted Domains or Dropped Domains are available for registration and can be picked up for just the normal regfee at your preferred domain registrar! All Domains have the typical SEO relevant data, like Number of Backlinks, Archive.org Birth Date and a lot more.