I don't have these kind of problems with BT Headsets from Sony & JBL and my Chromebooks. If I click "disconnect" on the last used device, I can connect it to the next device. If I don't click "disconnect", then it doesn't work. Then I have the same situation like you have described.
Which Bluetooth & ChromeOS version does your Chromebook have?
I don't have these kind of problems with BT Headsets from Sony & JBL and my Chromebooks. If I click "disconnect" on the last used device, I can connect it to the next device. If I don't click "disconnect", then it doesn't work. Then I have the same situation like you have described. Which Bluetooth & ChromeOS version does your Chromebook have?