Sorry to dredge up this old thread, but I've discovered that Chromebooks can run Calibre
AND connect to eBook readers. I've successfully set up Calibre on three Chromebooks, all work with DeACSM and DeDRM with Kindles and DRM'd ePubs. I don't know if changes in ChromeOS allow this, or if was just my ignorance in the original posts.
At any rate, if you have an Intel-based Chromebook and it's new enough to run Linux (most do now) you can install Calibre in Linux and it's completely functional. I still use Debian 10, which doesn't support the newest libraries so I can't run the 6.0.x Calibre versions on the Chromebook. So I installed 5.44.0 instead. Fortunately 5.44 supports the newest versions of DeDRM and DeACSM — so I'm not losing anything (that I know of).
To install Calibre 5.44 in in Linux in a Chromebook, just copy the following into terminal and ENTER...
sudo wget -nv -O- https://download.calibre-ebook.com/linux-installer.sh | sudo sh /dev/stdin version=5.44.0
I cut out the
sudo -v part of the command (which prompts for a password) because Linux in ChromeOS doesn't understand sudo passwords. I don't know any other way around it.
Once installed, an icon will be set up for Calibre and for each of its companion programs. It can be pinned to the shelf if you want.
De-DRM and DeASCM work normally. It's connecting to the eReader that takes a little bit more work, especially when hooking up the eReader for the first time. It has to go through two layers (which is my way of visualizing it, anyhow).
This is what you do the first time only (much easier the second time)...
1. Start Calibre
2. Plug In the eReader
3. When you get the Connection Notice, Click link to go into the File Manger
4. Right-click on the Reader (or double finger click) and choose "Share with Linux"
5. In Calibre, click on the Connect/share icon and choose "Connect to folder."
6. Click on "Other locations"
7. Click on "Computer"
8. Click on "mnt"
9. Click on "chromeos"
10. Click on "removable"
11. Click on your Reader and click "OK"
12. The device will come up. Click on "Device" and wait
13. Use as normal to transfer files
14. Eject the device when done, but do NOT remove the USB cable until...
15. You go to the File Manger and Eject it there also
The second time (and following), these are the steps...
1. Start Calibre
2. Plug in the Reader (wait for the connection notification)
3. Click on the "Connect/share" icon and choose "Connect to folder"
4. You Reader should already be highlighted, just Click OK
5. Transfer files, etc. as normal
6. Eject in Calibre
7. Eject in the File Manger
Sorry I didn't get this right the first time. A cheap Chromebook might be the answer for people who are having trouble connecting eReaders to newer Macs or Windows 7 machines. The only issue I can see is that many of the newer Chromebooks only have USB-C ports, so you might have to look for an older one that still has at least one USBmicro port. Otherwise you'll have the same problems newer laptops have. (Or maybe adapters can take care of this?)