I have a Libre 2 and also sideload everything through Calibre via USB, which can be rather laborious and was somewhat hit and miss, although it seems to be behaving itself on the latest Kobo FW.
Less laborious might be to install BookFusion on the Boox Page, and the BookFusion Calibre plugin. Then your book collection is stored in the cloud, and is available on the Boox (plus any phone/tablet with the BF app), without the need to physically connect it to the PC.
It's not enough for me to switch from Kobo to Boox, but if I was in your position, this might be something to consider, although there's a small BookFusion subscription involved.
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