When to buy Craftsman tools
I know the answer for a lot of folks is "never".
But mixed in with the rest of my tools, I have a lot of stuff I bought at Sears. Not only that, I know I'll buy at Sears again. I even did, um, last week.
Yes, it's true that a lot of Craftsman tools, especially power tools, have weird gimmicks in place of solid foundations. The people choosing which tools to sell apparently believe that weird gimmicks will sell more tools than quality. For a certain audience, they're right - occasional users, folks just getting into using these tools, and people who learn about tools primarily from advertising. For other audiences, a few failures and it's never again, or never even the first time.
The first few Craftsman tools I bought - largely sanders - felt like a big step up from the Black & Decker stuff I'd used for model railroading. (Okay, some of them were actually rebranded B&D. But at least it was better stuff than I'd bought before.) They took abuse well, starting out on floor refinishing and similar projects. All of them are still going strong. I expect I'll keep my 3x21 belt sander, actually a rebranded Ryobi, for a long time to come. I recently gave away a pair of orbital Craftsman sanders, ten years old, but still working well, because I'd bought other better sanders that could do more things.
I've been less delighted with the Craftsman Industrial dovetail jig, though I've made it work a few times and have concluded that it's at least worth the battle to make it work. I'll have more on that here eventually. The one Craftsman router I own has done okay, though most of what it's dealt with is dovetails - not very demanding work. I had a Craftman tabletop drill press for a short while that did well on some difficult projects, but gave it away when I finally found the drill press I'd been looking for. Generally, Craftsman's manuals have been as bad as any I've seen, though bad manuals seem to be almost a requirement for sellers of tools.
The Craftsman machine tools and toolboxes I've bought have all been fine. A good ratchet set is a pretty normal thing these days, and the wrenches - except for one crazy strap wrench - have all been fine. Pliers, screwdrivers, retaining ring pliers, all the tools I use to maintain my power tools, have all been great. I'll happily buy those again. The Craftsman shop vac I have is loud and obnoxious and lies about its horsepower, but is what I expected of a vacuum at that price. With the Dust Deputy and a new filter, it even has great suction. So that's okay.
In tools I actually apply to wood, though... hmmm. I think I'll mostly buy Craftsman for single-purpose tools I don't plan to use very often. They work, but they usually feel strange. Vibrating, or flimsy, or loud in all the wrong ways. There's usually an obvious weakpoint that makes me cringe, like the collet in that router (a 315.275000) router which screws into the bottom of the shaft. The depth adjustment seems to work for me so far, but not for other people, who've seen the bit drop during a cut. I don't think cutting dovetails will stress it out - I hope not.
The belt sander, though, has turned out well so far.