I've just recently gotten OpenVPN and SSH working on my Chromebook and it is fairly decent, though with some limitations that make me wonder who is really paying $1,100 and up for a Chromebook...
I got one of those crazy HP 13 chromebooks, a Pixel-level device that at the time a few months ago was really the only available option more recent than the Pixel. I ended up finding it on Woot for $520, instead of nearly a grand.
It has the high res display, charges over USB-C so I can use the same charger for my laptop, chromebook, phone, and Fiance's laptop. The device is nice.
The OpenVPN was not TOO bad to set up, but you seem to only be able to have one VPN active at a time. So I can connect to either the office OR the data center OR my personal network, where my laptop can connect to all of them.
The SSH works great, but doesn't have an SSH agent so copying from one remote machine to another doesn't really work. It looks like there is some agent option but I haven't gotten that working. One nice feature of the SSH program is that it can map the remote system as a local Chromebook drive, so I can drag and drop downloaded files when I need to.
For programming I'm looking at Cloud9, which I've played with in the past but never seriously. Probably will just end up SSHing to a box and running vim, I do very little development.
For running Ansible sysadmin tasks, I'm either going to have to go into my desktop and set up an SSH agent to handle the connections to all the other hosts, or use Rundeck once I've committed and pushed the Ansible changes.
So, 90% of what I NEED a laptop for at home (something broke at work, working on personal servers/network), the Chromebook will do, though not quite as nicely as a laptop.
Also, I'm using Enpass for passwords, and on the Chromebook I'm using the Android app, which kind of sucks compared to the Linux app version.
The comparison is that around the same time I got a Lenovo T470s running Linux. Also has high res display, also is tiny. It has something weird going on with the mouse buttons where after a suspend they sometimes "stick".
The Chromebook is less expensive, though not really disposable. The $250 chromebook I tried really kind of sucked.