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Have you considered keeping the Windows machine you are replacing for win-specifc stuff and getting the chromebook in addition?
My wife worked this way for the past few years until she got her new 2-in-1: She left her old windows laptop running upstairs sort of as a server, for DRM books and a few other functions (like running her die cutter machine), and would remote into it from her Chromebook to do stuff or get files when she needed to, but 90% of what she did, the Chromebook was it.
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