The beginning of the end was when they stopped pushing their in-house Kenmore appliance brand and started selling all the other brands -- as if they could compete with the discount sellers. Now they've spun off their iconic tool brand. There's nothing left.
My last interaction with Sears was "less than optimal".
Earlier this year we needed a new washing machine. Our needs by this time are not great. Hemmed and hawed, "who can deliver", etc. Eventually the wife found something on the Sears website that looked OK. I dug up my Sears login, and ordered it, with delivery + disposal of old unit.
It showed up on time, when they said it would. But, the delivery guys told my wife that the hose connection to the old washer was corroded to the faucet, and they just left. (it took me longer to find my channel lock pliers, than to get the connection off. Five minutes, max.) They left the basement door off its hinges, for my wife to remount. And, of course, did not haul off the old unit.
I eventually got a live voice at Sears. Bless here, her English is better than my Hindi, so I was able to communicate the problem. She got someone else to come out, a couple weeks later. By which time all that's left is disposal of the old unit.
They keep dunning me for a maintenance contract, but never did email me for a satisfaction survey.
So, yeah, Sears ain't what it was when I was a kid.