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.
Answer: Yes. For a vast majority of domain names that expire (greater than 99%+), the rules and processes listed above are valid. However, there appear to be exceptions to these rules. For example, registrars “warehouse” or take for their own domain name portfolios some domain names, and other domain names a renewed even past their expired or redemption periods. In addition, there is at least one registrar that does not have an auction partner, allowing expired domain names to simply drop and be available for hand register.
Now, a lot of times these great domains that have pending delete will get snapped up in a flash. Okay? You want to use the same system that’s 500,000 domains so you can always sort them by whatever you want to do to make sure you’re only looking at quality domains and look at the link profile the same way. Once you find one that you like, you can’t just sit on your computer at Go Daddy and wait for it drop on 6/14 and expect to get it because there’s going to be a lot of other people gunning for that domain. You actually have to use a service like Snap Name.
 On April 11, 2016, SnapNames (owned by Web.com) and NameJet (partnership between Web.com and Rightside) combined resources on pending delete/dropping domains to better compete with other drop catching services. Going forward, backorders placed on either platform for pending delete names will go into a common backorder pool and will be fulfilled either by NameJet or SnapNames depending on which platform the backorder was placed. Pending delete names that have multiple backorders will be placed in a common private auction accessible to bidders from both platforms to participate in the live auction. Minimum bid increments and proxy bidding rules for NameJet will be modified to match those of SnapNames. Registrar expiry, and direct lister inventory will not be affected by this integration.
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?
Lately I've noticed a lot of questions in Q&A centering on purchasing expired domains. A lot of our members have expressed interest in buying old domains for a variety of prices (some are cheap, some are going for upwards of $50k) and want some advice on what to do with the domains once they've been purchased. I'm no domainer, nor am I an expert in such a business tactic, but I generally recommend one of three different options for an expired domain (and would love to hear more if you've got any).
The following TLDs are now fully supported with a deleted list and a droplist (pending delete list). .hn, .ht, .rw, .cr, .gl, .gy, .gs, .om, .qa, .ir, .pe, .com.pe, .tc, .ky, .th, .co.th, .ke, .co.ke, .uz, .kz, .pm, .re, .tf, .wf, .yt, .sx, .gd, .gi, .kg, .mu, .im, .ug, .sb, .tl, .st, .sm, .so, .sn, .pf, .nyc, .cloud, link, .ms, .mk, .af, .bi, .pr, .com.pr, .nf, .nc, .dm, .bo, .ki, .iq, .bj, .am, .as, .ax, .fo, .mg