Ultimately, I was left with a semi-automated process of scraping sites and running an intricate series of processes to come up with a list of expired domains that I then had to evaluate by hand. This meant I had Majestic and Moz open to check the backlink anchor text and Archive.org to check for obvious spam for every single possible domain. The process was excruciatingly slow and tedious, but absolutely necessary to find domains that would be suitable for building out.
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?
Your best chance of getting it is contacting the current registrant and negotiating to buy it. After that, your best chance is buying it in auction or finding it listed with a “buy it now” price at a marketplace. Your other option is to find a broker who can negotiate on your behalf (if the domain name sells for a few thousand or higher…brokers likely won’t have the time or inclination to negotiate smaller deals).

The database also gives us the chance to analyse Whois, IP, NS, MX records and website content of every domain and to offer unique investigation and brand monitoring services for which websites like Whois.Domaintools.com charge a lot of money. With the tools we have developed we can offer Reverse IP, Whois investigation and B2B research in bulk at a world class quality/price ratio.

However, what do you think about buying expired high PR domains and creating local directories, business reivew, and event calendar sites that actually provide a value to the community? Then include a sponsored link from local business that is trying to rank? Do you think a method like that is a. morally soluble and b. viable long-term because it creates value?

The better quality links (From Google, Wikipedia) that a website has the higher will be its domain authority. New websites start with a ranking of one, and as the number of links increase the domain authority rises. For example, a sports website that has links to sports newspapers and sports reporting sites will have a higher domain authority than a sports website that only has links to other sports and sports blogging sites.
The dropdate for the following TLDs is not verified. Domains might drop earlier or later: .eu .cat .travel .ae .af .as .at .aw .be .bg .bi .bj .bo .bw .cl .co .cx .cz .dk .dm .es .fi .fo .fr .gd .gg .gi .hk .hr .hu .ie .io .iq .ir .je .jp .ki .kz .lt .lu .lv .md .mg .mx .nl .nc .nf .no .nz .pe .pf .pl .pt .ru .sg .si .sm .sn .so .st .su .sx .to .uk .uz .za .berlin .cloud
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