Looking at your trend, you've got $500 laptop / 2 year, or $2000 laptop / 5 year, which reduces to $250 laptop / year vs $400 laptop / year. Getting low cost laptops isn't necessarily a worse financial outcome, although it depends on how fast the processor updates are moving; when a 2020 intel cpu is about the same as a 2015 intel cpu, it would probably have been better to pay a little more in 2015 for a faster one; when a 2015 intel cpu smokes a 2010 intel cpu, incremental updates every year or two mean a low cost 2015 cpu is probably better than a high cost 2010 cpu. Plus, you get a battery refresh (even if it's small).
I think there's more junk at the low end to avoid, but it's not as if the high end doesn't have a lot of junk to avoid. Either way, you have to do careful shopping.
It's like just my opinion, but a lot of higher end laptop spending seems to be on increasing the screen's DPI, which is then run with scaling, at the cost of more CPU, more RAM, more GPU, and more software BS. Buying a cheaper laptop with fewer pixels that just runs 1:1 saves all that extra computation and BS, and maybe looks a bit less nice. Sometimes glossy screens are reserved for the high cost laptops, which is like wait, I want a matte screen, so I have to save money to get one, great!