Purchase a Chromebook or "regular" laptop?

I think the biggest concern with chromebooks is their “expiration date.” Each model ships with a specified EOL date based on when it was certified, whether it’s a $1000 device or an $80 device. If you go with chromebook, make sure to check this date before you purchase anything because it essentially becomes e-waste at that point. It looks like it’s set somewhere around 8 years, but if you buy a model from 2019 that 8 year clock started ticking in 2019, not on your purchase date.

of course, it’s google, so “8 years” can also mean “until they feel like pivoting towards a new fad.”

Depending on how heavily you weight your use cases, different options may be best. If you really like using something in tablet mode, an ipad is a solid bet and the base model is relatively affordable.

Chromebooks can be jailbroken, using dev mode you can flash them with linux. You’re going to be limited by the (typically) eMMC storage and processing power though, they put really cheap components in these typically. Not sure about battery life but I know S0 (“modern standby”) sleep is plagued with problems that it seems like only mobile operating systems (including chromeOS) have solved so far. But if your device charges with USB-C, you can always use a battery bank as a bridge between wall outlets (there are also power banks for many other charger styles, though they’re typically more expensive and more specialized).

I think when you start getting into chromebooks with stylus support, better storage, more than a “basic” processor, an ipad with keyboard/stylus accessories will be a similar price. Or you could try buying a used laptop on craigslist/marketplace and flash it with linux to improve performance. You’ll probably be sacrificing a lot of the “fancy” stylus support if you go with linux though since it’s typically very proprietary (but that’s just a guess).

You could also go the opposite direction and flash an older device with ChromeOS Flex. It’s super lightweight because of the normal resource constraints in chromebooks, so it should run nicely on most machines, even very dated ones. I think the primary concern on this side would be the age of the battery.

I don't have experience with Chromebooks specifically, but I did buy myself a craptop: an Asus E410M. It was the cheapest new laptop I could find. It came with Windows 10 S that could barely run; each click took several seconds to register. It was a real pain due to missing wifi drivers, but I eventually got Kubuntu on it, and now it is my daily PC. I use it for streaming, text editing, and browsing. No touch screen, so likely not what you're looking for. The issues I had:

• Mine only had 64GB of internal memory. I had to put on a 256GB microSD. I started with the cheapest I could buy, but the read/write speeds were so painful that I upgraded to a higher end card.
• It gets hot while streaming video
• The battery failed 1year and 3 days after I bought it. There are no official battery suppliers for my laptop so I had to go with a sketchy 3rd party replacement. It's been a year since then, and no repeat issues. I typically get more than a day of use between charges.

Overall, because of how physically light and convenient to use it is, I find myself rarely using my beefier computers.

Will this be your primary device, and do you have secondary machines for more intensive purposes?

Chromebooks work very well for cases where you do most of your work in a browser, or as a thin-ish client. For all the use cases you listed, any decent chromebook should work. I have a few chromebooks around the house for thin-client use (Chrome Remote Desktop to lab machines), and use an enterprise device for work (HP Dragonfly), and have been happy with them.

In my experience, ChromeOS is relatively low-touch to maintain a decent security posture (outside of the Google-links), and have pretty clearly defined support windows. This makes them a good low maintenance option if you don't need heavy customizability and can work within the confines of ChromeOS. I would consider if your note taking and other programs would work well as either Android or Chrome extension options though. If you need to run the desktop programs from a Linux container that is possible too, though might be a little higher friction.

As mentioned, there is a built-in way to run Linux containers within ChromeOS, as well as (I believe) ways to run Linux natively if you want. I have not tried the native option, so I can't comment on the compatibility and experience though.

What’s your budget? Do you use Android or iOS for phone?

Id recommend going with a “normal” laptop. Most of my laptops recently have either been from Framework or Apple.

What specifically do you find attractive about Chromebooks?

Generally speaking I'd recommend a regular laptop. If budget is a factor, go for a proven model that's a year or two behind the curve either refurbished or used. Regardless of if it's running Windows, Linux, or macOS, regular laptops are immensely more flexible which can help accommodate unexpected needs and repurpose the machine down the road. Official support is much lived for those operating systems too — Google has a history of dropping support for Chromebooks surprisingly quickly.

I'm a big fan of Chromebooks, and I've been using one as my primary device since 2017 (with the Google Pixelbook, in fact). I'm currently using the Framework Chromebook, which is a beast and probably way overkill for what you're after (not to mention doesn't sport a touchscreen).

There are some downsides, mainly for me that it is heavily tied to the Google ecosystem.

Yep, and there's not really any getting away from that. What you can do if you don't really want to play in the Google ecosystem is set up a new non-Gmail identity-only Google account and use that as the login account for the Chromebook. That way anything that happens on there won't be associated with your other accounts or services.

Can chromebooks be easily jailbroken and run a lightweight window manager on Linux? If so does the device retain its battery life okish?

Chromebooks can't really be easily "jailbroken" can be run in developer mode which would allow you install a Linux chroot environment which would let you switch back and forth between Linux and ChromeOS on the fly, but the primary project for that was abandoned in favor of the built-in Linux development environment. This is pretty easy to set up and manage, and lets you do Linuxy things without breaking ChromeOS's security mechanisms. You're not going to get an alternative window manager that route (well, you can but it's going to be essentially a nested KVM session and that starts to get gross), but it does give you access to basically any Linux apps or utilities that you could want to use. I'm a heavy user of the Linux environment on my Chromebook, and it's more than handled my needs.

(I also recently removed the firmware write-protect from my Pixelbook, flashed a custom UEFI firmware, and installed Fedora on it, replacing Chrome OS entirely. It works okay and will come in handy for the small handful of use cases that can't be handled by the nested Linux development environment (mainly regarding raw access to hardware devices), but the battery life and stability have both taken a hit. I wouldn't have done it except for the Pixelbook coming up on its automatic update expiration next year.)

Could I still use a stylus with the device?

Depending on the device, absolutely. Most Chromebooks (my Framework excluded) have touchscreens, and many of those support stylus input devices. Some might use different stylus technologies though so it's important to check the Chromebook specs against the stylus you're looking at.

Would I be better off buying a cheap laptop and install linux on that?

Honestly it depends on your needs (and comfort with Linux). Based on the use cases you described I think a Chromebook would be a good fit, and you're unlikely to find a laptop that will run Linux as efficiently and stably as a Chromebook runs ChromeOS.

Finally I've read that Google cancled their Pixelbook 2 last year. Has there been any updates or rumors of it coming back (I tend to like Google's hardware)?

Nothing that I've heard lately, unfortunately. That OG Pixelbook hardware was brilliant.

[Edit: completely forgot about the dev mode approach as a form of "jailbreaking".]

Honestly, it sounds like you want a tablet with just a little bit more power. Why not buy a microsoft surface or some other kind of tablet-esque laptop? You get the benefit of having a windows device and a tablet.

All the chromebooks I've seen are cheap junk. The exception would be the higher end machines like @codesplice mentions with the Framework... but those cost as much as decent laptops or ARE decent laptops just with chrome OS.

IMO you've got a few options, in no particular order.

• iPad for stylus support. The apple pencil destroys the one that the MS surface has... or at least it did a few years ago when I last looked. SSH via ssh apps works just fine. You will want a keyboard though.

• Macbook Air if you're more into having a keyboard but want something almost as portable as an iPad. Battery life is insane, performance is excellent considering its passively cooled. Doesn't even get hot. Linux support is not daily driver ready.

• Framework if you want to run linux/windows and care about repairability

• Used laptop if you want to be cheap.

A Real twist...

I got a steam deck, and dock... Got a USB hub/switch.

I switch to desktop mode and using linux (First time in a while) And i'm really finding it so much easier than latest windows.

Use it as a desktop and play/watch on the go!

(I know this is not real solid advice, but still plausible!)

A used Thinkpad is the laptop I recommend to everybody. A model like the T460 is built like a tank, fast, upgradable, and most importantly (to me at least) really cheap.

My students use them at school. They're not bad if you're just typing stuff and you have to be able to afford hundreds of them. but I wouldn't want to have one as my only computer.

I went through a phase where I wanted to de-couple from Google’s ecosystem so for me the Chromebook would be put. That’s a personal thing though.

You could also throw a tablet+keyboard into the mix for your stated use case.

If you’re willing to spend the money, a refurbished MacBook Air can be had for under $1,000.

Even the older M1 MacBook Air will give you excellent battery life, performance, and build quality. It will last a long time. I have multiple friends using near decade old MacBook Airs that are still going strong.

If you want cheap, I've been seeing deals for refurbished Dell Latitude 2-in-1 laptops in the $200-300 range, direct from Dell. Seems like this would fit all your criteria, including stylus support (sold separately). A bit of a crapshoot on condition, though.

If you do get a cheap Chromebook close to it's expiration date, you can eek a few more years out of it with Chrome OS Flex or the Brunch Project if you're willing to flash a new bios. You may also want to take a look at a used iPad if you want something dead simple with years of support, that isn't 100% dependant on Google.

In my experience troubleshooting my dad's chromebook, they're just awful all around, and I would definitely just buy an old model refurb laptop, it'll be way cheaper with more storage to boot.

I looked into installing linux on it and it just wasn't worth it from what I remember of all the hoops I'd have to jump through.

I own a notebook from 2020 which I bought for 900€. Recently a friend of mine asked me which laptop she should buy for university, to which I replied to buy a Lenovo T480 from eBay.

She bought one for 180€ and I set it up... it is a far better device in terms of usability than mine and I even thought about selling my notebook and buying one myself. I can reassure you: their reputation isn't nonsense.

As long as you don't want to play high-end games or do heavy rendering work or so, that laptop is honestly enough. There's no need to buy something new "for more performance", as for what you do paying more will deliver diminishing returns. Apart from that they're actually far more upgradable in case something "isn't right". The i5 8th Gen model will already deliver sufficient performance and with an SSD it'll load fast.

So: (used) T480 + drawing tablet.