For under $300 at this moment and having an i3 and 8GB, it is hard to beat Lenovo Flex 5i 13 Chromebook 2-in-1 Laptop, Intel Core i3-1115G4, 8GB RAM, 64GB Storage
The Lenovo Flex 5 13" at costco is an amazing deal. $300 for an 13", i3, 8 RAM, 128 storage, touch screen, foldable, speakers facing up when in laptop mode for good sound.
If you can't shop at costco then amazon has similar one. It's $80 more with 64 less storage, but still more than enough for just about every average person.
https://www.amazon.com/dp/B08YKFTZH6?psc=1&ref=ppx\_yo2\_dt\_b\_product\_details
I used to replace ChromeOS with GalliumOS and it was great, but that is nearly the last thing that I'd do these days ... if you want a reasonably priced Linux laptop, just buy a Windows laptop, replace/augment it with Linux, and save a lot of hassle.
If you wish to run a Chromebook with Crostini (as I do now), then I'd suggest getting an i3 (or better), 64 GB of disk or more, 8 GB RAM or more. Something like Lenovo Flex 5i, i3-1115G4, 8GB RAM, 64GB Storage for $303 at this moment.
On the Chromebook, I'd then install https://github.com/joedefen/crostini-kde-setup and run Debian "unstable". Then use the Chromebook/Chrome for what it does best, and augment it with the Linux apps you need (and that provides a good starter set).
The Flex 5i is a good machine for less than $400
https://www.amazon.com/Lenovo-Chromebook-i3-1115G4-Processor-82M7000SUX/dp/B08YKFTZH6
>re: I'm a programmer by trade and a nerd by heart.
Copy that. Then you'll almost certainly want to run Linux, sooner or later. To run Linux well, my minimum specs would be an i3 (10th gen), 8GB RAM, 64GB disk, 1920x1080. These usually can be found for $300-$500 (e.g., $300 refurbished Lenovo 13.3" i3-10110u 8GB Ram 128GB SSD) or $400 Lenovo Flex 5i i3-1115G4 8GB RAM 64GB Storage 13.3"). You can easily spend as much for a much less capable Chromebook, or just go for the $200 variety that browses OK.
If you go with smaller than 13" screen, "programming" is very constrained (14" is my ideal). Over 14", then you usually get un-centered keyboard/trackpad to fit the numpad which I detest.