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$300 is a really difficult price point for what youre asking for new. At the price, youre in the chromebook range, where even the windows machines are going to be as barebones as possible.
You want to step into the used market if you want customizable for $300. Getting something good thats a few years old like an lenovo carbon x1 looks possible, and they are a dream to update. The above supports linux with no issues.
I see. There's not much of a choice outside the used thinkpad range then. Very well. Thank you
Yes. This is the way.
Honestly, the value proposition of old business computers is almost unbeatable.
Yes, it's not the most recent hardware, but decent enough, especially the chonky boi ThinkPads are very easy to repair/upgrade and built like tanks (though only Russian ones, they barely withstand an RPG hit, which is a shame).
Could you suggest a few models? I'd be fairly interested in older business laptops especially if they are a viable alternative to the thinkpad line (never a bad idea to have more choices!)
Dell Precision, HP Probook for example. There are probably more, but these are the ones that I know of.
Cheap Chromebooks tend to break just like other cheap laptops. The only difference is that the OS may feel more responsive initially.
Upgradeable parts = non-soldered RAM and SSD?
I can recommend minifree.org - this is a shop from Leah Rowe, who is the lead developer of the libreboot project. That is a (more secure) bios alternative, related to coreboot.
I bought my Thinkpad T400 from there, some 6 years ago or something. I am still writing on it and i can highly recommend it. However, today i would buy a smaller form factor. so 12,8° instead of 14°.
So it is kind of heavy compared to a macbook air and not the fastest machine, but you can get your stuff done. And it is really really durable, which is the reason i bought one of the older thinkpads.
Around $300, there would be the libreboot 820: https://minifree.org/product/libreboot-820/
And with minifree.org you can be sure that the linux/libreboot/coreboot support is really great. Because: since Leah is a developer, she testes everything beforehand and fixes problems when she notices it. So i would recommend to describe what you would want to do. For instance, initially i wanted to use a encrypted harddrive and i had installed the grub variant, but later upgraded to libreoot with seabios. This was much better and fixed the problems with my encrypted harddrive. But i suspect leah would have found out and fixed that already, had i told her that.
Also for instance, seabios has better openBSD support.