I wonder how much of it was learning the wrong lessons from the relatively quick decline of Service Merchandise [1]. While a more "regional" competitor to Sears, Service Merchandise remained in the catalog game longer than Sears, was possibly the most successful catalog merchant of the 80s and 90s (depending on who you ask, and again some regional biases), and was also relatively active on the early internet (making millions apparently in internet sales in the early 1990s, ahead of Amazon).
Every article I see about Service Merchandise's decline blames the catalog business (despite doing well in internet sales) as being "too old fashioned" and the root cause, and certainly that's what people seemed to be thinking in the 90s (again, wow how they ignored those internet sales looking at the quoted figures). I'd love to see a better retrospective on the company's 1990's management given we saw Amazon succeed.
Maybe more so than Sears, the fact that Service Merchandise didn't compete better with Amazon is fascinating. Service Merchandise and Sears thought they were competing with Circuit City (dead), Wal-Mart, K-Mart (bought by Sears, dead), Target, rather than each other in the 1990s, and Amazon was left almost entirely uncontested to eat Sears and Service Merchandise's original core competencies.
[1] https://en.wikipedia.org/wiki/Service_Merchandise