My father-in-law has a split system labeled "Kenmore" installed at his house, circa 2004. I looked closely at the data plate, as years gone by, Whirlpool built a lot of stuff for Sears (and may still do so). This one was Goodman Manufacturing.
I'd rather go with a reputable contractor selling Goodman than Sears selling Kenmore, personally.
We've gotten a price on a Rheem product and Sears has given us a price on a Kenmore product. They claim it's a Carrier system with the Kenmore name. Any thoughts about the Carrier brand as a secondary question??
Really depends on who's installing it. All brands can fail. A proper installation is more important. Who did the load calculation to determine sizing? Who looked at ductwork and (possibly) made suggestions? I wouldn't call Kenmore a Carrier labeled Kenmore. I'd call it an ICP labeled Kenmore. Look at Carrier's equipment line and compare it to Kenmore's. Carrier has more to offer in my opinion (Infinity system, controls, accesories, etc.).
In all honesty it was Sears that took the time, did the load calculation and really talked about all of that. The local contractor (from whom I've had some minor work done before) was literally in my home for about 20 to 25 minutes, wrote up an estimate and left. The local contractor installs Rheem products, a brand I certainly would trust. I just felt like he didn't really take the time. In addition the Rheem man wants to reduce the size of my furnace from my current 100,000 BTU unit to a 75,000 BTU unit. He said my current furnace is actually too large. Sears, after the time they took and all of their calculations, said the 100,000 BTU unit is a better fit for my 1950 sq. ft. home. I'm hoping to get a third estimate within the next couple days. I'm actually trying to get different brand names for comparison.