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This is very situational. I’m not a contractor, but I spend a significant portion of my time doing hobbies that require power tools. I don’t need a drill that will last for an entire day at a jobsite. Ryobi works fine for me. On the other hand, I wish I had never spent $600 on a cheap planer; I knew I’d want a better one eventually, and sure enough, I found a need to upgrade after a few years. Now I’ve spent $3600 on planers. I could have just gone with the $3k one and saved myself $600.
If I’m going to use it once, I borrow it. If I’m going to use it every few months, I buy a cheap one. If I’m going to use it every week, then it’s worth it to me to buy something I can keep for at least a decade or two.