Mark:
Having been at this for 30 years I think that from my perspective anyway, in the old days Craftsman stuff was the only game in town and so we used it. I always found it odd that Craftsman in particular always seemed to be great at taking something simple and making it more complex than needed. For example, I have a 35 year old 1/4" Craftsman Router that had custom micro switches in the handle to turn the thing on and off. They clogged up with dust after about 6 weeks and so I was forever sending away for new ones because they were designed for that router and were not available as stock items. Well after spending $20.00 for 2 of them more times than I can count I drilled a hole in the housing and replaced the microswitches with an on/off toggle switch. That same switch is still working today.
In the years since I purchased that router several things have changed in the tool market. First there is far more variety today than 30 years ago. We are also now enjoying all the great thinking that over the years has improved our tools dramatically. Look to any of the major brands to see evidence of this! Things like locking arbors or variable speeds better fitting handles, lighter weight more powerful and more efficient motors and on and on.
I think one of the other big changes and this one plays into your question directly is the homeowner or DIY movement in tool manufacturing. Craftsman and other companies like DeWalt etc. have all learned that the homeowner won't pay $250.00 for a circular saw or a drill like the trades will. So the consumer version of these products are built to a price point. You will find plastic gears, nylon bearings and weaker motors in them and in the hands of the homeowner who hauls the tool out now and again they will last. For the professional who depends on his/her tools 5 days a week they burn up,strip their gears and generally go slower! So I think one needs to consider the markets and if you are a pro and use your tools continuously Sears stuff probably won't cut it. If you're an occasional user the cheap stuff will do in most cases. At least until you step up to a professional model and then there is no turning back!
My grandfather always told me to buy the best tools I could afford. That way you only buy them once! I can tell you that any time I've broken that rule I have paid for it with broken, incapable tools that have in the end cost me far more than the price of the high quality tool.
Enjoy your purchase!
CJ