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.