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My PC is set up to load Garmin Express when it detects my Nav VI. Then it checks the version of Garmin Express and offers to update itself if needed. Once it's done that, it checks the Nav for firmware and map versions, and if the are newer versions it asks if I want to upgrade them.
I don't find the process of keeping current to be onerous at all.
If I could plan routes on my iPad Pro and send them to the XUMO XT GPS via bluetooth or cloud transfer, I would be a lot happier! (Old Montana has no bluetooth)