Bought a cheap power drill, like "I can't believe how cheap this thing is". It broke after 15 minute of usage.
Never go cheap on tools.
Always go cheap on tools you are trying out.
If 6 months pass and you are still using it, and notice it not being enough for your use, then get a quality one.
I've seen many quality tools that have been used once or twice after years, bought out of impulse.
This is really the way to go. Most "cheap" tools will offer the same or similar performance to the name brand ones or like you mentioned you'll splurge on a nice one and realize you only need it for one or three jobs and the generic brand would have sufficed. I've been buying harbor freight tools for years I can think on one hand the amount of tools that have broken and it's usually not because they weren't up to par for the right job but because I did a hackjob and macgyvered them for something they were never meant for.
I bought the $15 HVLP spray gun and it performed very well for years. When it finally could not be cleaned up and repaired anymore, I just bought a new (now $17) one and have been using that one for years, too. $32 for a decade worth of spraying paint.
Can you point me to that HVLP gun for under $20. I have purchased two different ones for ~$100 each and they make this list of "things I regret"
I also subscribe to the buy cheap, if you use it alot and it's not working out buy a much better model. I've done that for years and have a hodgepodge of brands that make me happy. The only exception is battery powered tools, I did some research, decided that Dewalt would be a good choice. I didn't want to have 10 different kinds of battery packs around, so picked the battery ecosystem and went from there.
And when I buy a wood chipper, my Fujifilm printer will be the first thing through it. I have wasted more time and supplies to get pictures that look like a 2 year old colored it. So sad.
I sometimes buy quality tools for a single job. Generally, I can complete a job at 90% of pro quality at 30% of pro prices and that includes buying the tool. So if it is really never going to be used, I can always resell online.
I think it depends on the type of tool. If it's a specialty tool that I don't expect to use more than once or twice, I'll go for cheaper model. On the other hand, if it's something that I expect to use a lot then buying a quality tool (possibly used) is the better route. All of my cordless power tools are Makita but my 2 Makita drills were both bought used. For hand tools like combination wrenches and sockets my default route is used SK Tools bought at yard sales, pawn shops, eBay.
Counter point I have a harbor-freight drill that has lasted almost a decade. I recently replaced it because I needed more torque.
If you're careful there are so, so many harbor freight tools that likely come off the back of the same Chinese factory name brands do. Their "professional" line is about 50-70% less expensive and performs as well. The impact wrench is better than a Milwaukee, and their professional torque wrench comes within tolerance to a Snap-On.
For someone who doesn't need a QA cert for insurance/licensing reasons harbor freight is a miracle. Likely because it's the EXACT same stuff. Nothing is made in America anymore.