One thing I've found, as an amateur woodworker, is that sometimes the cheapy tools are okay, but only if they'll get light use. While installing radiating barrier in my attic, I overshot the duty cycle of my el-cheapo B&D staple gun, and the coil/solenoid got hot enough to melt the plastic it was mounted on, just enough so that it "jiggled" around within the housing, and therefore could not apply maximum force to drive the staple.
I have bought and used some Harbor Freight stuff, and it's adequate for occasional use, but accounting for duty cycle, and for precision needed, sometimes it's better to spend more. I certainly wouldn't buy HF or consumer-grade tools if I was a contractor...
I have an iron skillet and griddle I bought at WM that I'll probably hand down to my heir, but I also bought a brand-spanking new 12" Lodge skillet off the clearance rack at Cost-Plus for $19.95. Made in America, and also likely to outlast me, and maybe my son.
Bought a mid-priced SS cookwear set from WM, which worked reasonably well when I had an electric range, but it doesn't work as well on the gas range, so will likely replace at some point. Have another PTFE-coated set I bought at Target years ago that is much better at heat transfer, but I really don't like using Teflon.
Don't spend that much on clothing, and use Kohl's 15-20% coupons, which I seemingly get once every week or two, for that. As long as I don't "outgrow" my pants, I keep jeans and jean/cargo shorts for years...
I've been buying more "American-made" stuff, which does usually cost more, but I figure it's an investment in keeping a neighbor employed rather than depending on the dole... Any extra cost works itself out, since I'm not your "average" consumer. There are companies that make jeans in the USA, and the aforementioned Lodge cookware is made here as well.
I once bought a Proctor-Silex drip coffee maker for $8, and used it for maybe ten years before it bought the farm. Doubt Proctor-Silex is anything but another name for "cheap Chinese crap" these days, but around my house the coffee maker gets a workout!