I have one. If all you ever want to do is browse the web, it's mostly fine. The chromevox screen-reader is not the best thing in the world, but once you learn to deal with it, it works OK. The main problem with Chromevox is that it isn't user friendly, and the way it's designed everything takes two or three times longer than it would with any other screen-reader. But it all does work, where work is defined as you can get everything done eventually without sighted help. Unfortunately, the documentation isn't the best, either; the shortcut keys you need are spread out over two or three different places, so it's a bit tricky to learn them all. The most important two that aren't listed in the chromevox documentation are search+f2 to toggle between the tray with wifi etc, and the app launcher, and search+f6 to toggle between parts of the browser window (the main content, the address bar, and so-on).

How old is your brother? If he's in middle school or junior high, a chromebook would be absolutely perfect to take to school and use as a note-taker, assuming the school has wifi. The battery lasts forever, it boots up and down extremely quickly, and Google Docs would be just right for taking notes and completing assignments. Also, it's small and light, so it can be easily carried on the walk to school, or on the bus. Plus, it's cheap enough that if it gets stolen, it sucks, but it isn't absolutely the end of the world.

However, come high school, he might take a programming course, a science course, or any other course that requires some desktop app. And then he's going to need Windows anyway.

If your brother is an adult, looking to get into, or stay in, the working world, then a chromebook makes a nice back-up computer. But it's just not capable enough to be a main computer. That's how I use it, in fact. The chromebook goes anywhere I don't want to carry a full sized laptop, or anywhere I want long battery life. It's perfect for writing emails outside!

Don't do it. Chromebooks are awful and ChromeVox equally so. They absolutely need an Internet connection to be of any use at all, and based on all the available forms of screen readers out there, Google definitely has the worst one available. If you want to stick to windows, grab NVDA if you don't have the money for jaws. Personally, I highly recommend getting a Mac and using voice over, but that's my own opinion.

ChromeVox uses very convoluted key commands for basic navigation, some of which use up to four or five keystrokes wear the same can be done with only one keystroke using Jaws or voiceover. It is very buggy, and in my testing has proved to hang quite a lot and become exceedingly frustrating to use, even on Google's own pixel chromebooks. It has a tremendous way to go to even scratch the surface of what Jaws and voiceover can do, and it's development is extremely slow.

I have no experience with Chromebooks, however there was a post about this a little while back which you can find $1 where I believe someone said something about some major accessibility problems with them. I would personally steer clear, what I would recommend is maybe getting a newer affordable laptop that's a little faster and get NVDA which is a free and awesome screen reader on it. That, or just flash a new copy of Windows to his old laptop which might fix the performance issues either way and then add NVDA.

Thanks everyone! It looks like it might not be worth it, from what you're saying. I always thought a Mac would be the way to go, but they're so expensive. Maybe I'll look into a Windows computer with NVDA. What hardware requirements to run NVDA? I only ask because I feel like Window-Eyes is a bloated program and the cheap desktop he is using is not powerful enough for it.

By the way, my brother is an adult and works in a occupational center, so his needs are mostly for web surfing, Facebook, YouTube and emails. Once I pick a program and computer, what is a good place to go to learn how to use it? I'm thinking he should be ok if he uses YouTube tutorial videos. Thanks again!