As for me, I don’t own all that many tools yet, so I have had fewer chances to make dumb purchases. While Dave has six tools of which he’s embarrassed, I only have three. And here they are:
3. Bevel gauge kit (via eBay). I wanted a bevel gauge. On the one hand, I didn’t want to pay out the money for a vintage Stanley; on the other hand, I was being a little too snooty galooty to go buy a new Stanley from Home Depot. I compromised by getting a kit – something I could make with my own two hands without really needing any real skill. Well something got screwed up in the assembly (go ahead, blame me) and the blade isn’t tight – even with a shim. Well, it looks nice hanging on the wall anyway.
2. Local chisels, scraper, wooden bench plane and spokeshave (okay, I’m lumping a few tools together here). These things are not embarrassing in and of themselves; what’s embarrassing is what I tried to do with them. The chisels, plane and spokeshave (Chinese made, poor quality) were as dull as any other you might get right out of the box, but I thought they were sharp and was frustrated by how poorly they functioned. And the scraper? I had read somewhere about how great scrapers were at smoothing the surface of wood, so I bought one. A paint scraper. And you know what? It didn’t really do squat to smooth my surfaces. Go figure.
1. Craftsman 14.4 volt cordless combo. This included a drill/driver, a dustbuster and a circular saw. The combo came with two batteries, and good thing! Each one held a charge for like 20 minutes it seemed. It was even worse (as you might expect) with the circular saw. Speaking of the circular saw, when I got it out of the package, the blade spun the wrong way! After searching the forums (and being berated by “real” woodworkers for buying Craftsman), I figured out that the wires were crossed between the motor and the battery receptacle. Easy enough to fix. Upon returning to Malaysia, I found that the batteries are just about entirely shot. All in all, a hideous purchase. I still have them, though I don’t use them at all anymore. My ryoba and bit brace do just fine; as for the dustvac, well I’m doing hand tool stuff now so it’s more contained and easily swept up.
-- Eric at http://adventuresinwoodworking.com