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@Velocio
I use a Garmin with Linux, which is pretty much the same experience as Chrome OS.
There are some issues.
Yeah you can work out routes on most routing websites, and export to GPX or some other format that the Garmin will recognise.
Yes you can transfer those to the Garmin and it will work wonderfully.
Yes you can update maps for free and other stuff really easy.
But... when it comes to something like a firmware update in the Garmin to solve some obscure bug that's affecting you. Well, now you're screwed. As Garmin Express is limited to only very popular OS's, and the web updater won't work as it only works by installing a listening service in Windows, etc.
The Linux and Chrome OS experience is that you can actually be in a far better place than most Garmin users 90% of the time, but that last 10% of the time will really bite your arse.
Oh, and the Garmin cloud stuff is fairly useless without their syncing software, so you'll be using something else like Strava or RideWithGPS to act as the web-based store of routes you've done, etc.