You have a gigantic time range here, more than one era.

They were the Walmart/Amazon of their time (with competitors Montgomery Ward, JCPenneys - take a look at a JCPenney lawn tractor in case you think they've always been just clothes and housewares).

But while WalMart may be regarded as low quality today, Sears was not in their heyday. As stated in this Washington Post opinion piece, "What Americans bought there was certainly not glamorous; one might even call it boring. But what it lacked in flash it made up for in reasonable prices and solid quality that lasted."

By 1900, Sears had been taken over by Julius Rosenwald. Rosenwald departed from Mr. Sears' habit of looking for the cheapest prices: "Rosenwald’s impact on Sears (the company) was immense. While Sears (the man) never paid much attention to product quality—he just sold whatever he could buy cheap—Rosenwald looked for the best products."

When he was getting to retirement age, he looked for a replacement that was in his 40's. He found General Robert Wood, who after his military career, joined Montgomery Ward in 1919 and then left for Sears in 1924. While at Montgomery Ward, "Wood also began to develop long-term relationships with the suppliers of the best quality products. Previously, both Ward’s and Sears had bought their goods one order at a time, negotiating the price on each order, pitting suppliers against each other. But Wood picked the best suppliers, worked with them to keep costs down, and committed to multi-year purchases. Ward’s giant orders saved suppliers the expenses of advertising and staffing a large sales force. Both Ward’s and the suppliers realized higher profits while Ward’s customers saved money."

Wood became chairman of the company in 1939, and remained in the position until 1954. "Wood understood, respected—even loved—his customers. He made it clear to the entire organization that only the customer could fire them. Sears’s ultimate responsibility was to discover, develop, and sell to the public the best products at the lowest possible prices. " (Same source, again)

The thing to remember with Sears products is that they sold many different brands, as well as their own, and the quality could vary - You'd find a bottom end blender next to a top end blender on the shelf. Even their own brands were often made by others. Their Free Spirit bikes, for instance, were made by Puch in Austria in the early days, and Murray in China towards the end. None of them would have been the top of the line, but the early one's were certainly decent. Their guitars, branded Silvertone, were mostly made by Kay and Harmony. Some were junk, and unplayable (I've owned two like that), but some, like the 1220, were quite good - even if it was ladder braced, which is less desirable.

Their tool line, Craftsman, was well respected into the 2000's.