Chromebook, Macbook, Windows laptop — I have them all, I use them all. Macbook is the best long-term. Chromebook is the biggest bang for your buck. Windows laptop is meh.
Chromebook. It just works. $220 Asus survived a couple years of kids abuse and its hinge wiring failed and display died. At that point it was out of warranty and not worth the repair. Beefed-up replacement, another Asus, in $500 range, works for my wife's tasks since 2019 and she's happy with it: it can flip the keyboard around, has touchscreen, etc. The OS ecosystem is very meh. Basic stuff works fine, but if you want any extra (image editing, any coding), you have to be ok with some inventive approaches or some compromises. I wouldn't buy premium Chromebook, because at that point the limiting ecosystem and OS not worth it. But up to $500-$600, it's very hard to suggest anything better than Chromebook. However, if your budget gets to $500+, consider iPad (see next).
iPad is actually pretty decent alternative to mid-range Chromebooks, depending on the circumstances. My parents prefer iPad over any laptop mostly for "can't accidentally mess it up into unusable state". Web browsing, taxes, you can do all that on iPad for sure. Me personally is a sucker for physical keyboards, and iPad+keyboard propels prices to uncomfortable range of Macbooks
Macbook. I've used a bunch of Macbooks for work. I have one personal Air with M1. Expensive, silent, fast, works great, great ecosystem, good support from 3rd party developers. If you're using other Apple products, they place nice together.
Windows laptop. I have HP, priced between Chromebook and Macbook, somewhere in $700-800 range but its performance is about as my Asus Chromebook that is 1/3 cheaper. The OS is needy, fans are spinning for mundane things. The only reason I content with it is that there's some stuff me or my kid need which works on Windows only.
Based on my experience, $300 Windows laptop is going to be not great. You mentioned you were happy with your previous Chromebook. I strongly recommend to buy Chromebook, you will get better overall result than discounted Windows laptop.