I couldn't figure out how to get the whole mapping to a drive thing to work a couple of years ago when I last had this issue and it's still over my head. Although I'm the most tech savvy in my household, I fear my tech skills are sub-mediocre compared to others on this forum. All I know is that I never have this problem with opening things from the external hard drive that have a significantly longer path than calibre does. I'm talking things that are saved to the Desktop folder and then have a few other layers of folders after that, whereas I only had Calibre inside my documents folder. I feel the character limit is archaic and that it should be done away with, but I suppose that's more on Windows to fix.
I ended up moving the calibre folders up one level to the user folder, which is where most of my other portable program folders are, but for calibre I really had preferred to have it inside my documents folder. I'm not happy with this arrangement of having to have calibre in a location where I don't want it and having to shorten other folder names in the path to names I don't prefer, but it's probably going to be less of a headache than trying to figure out any weird tech tricks that really shouldn't be needed. I've made a note to update the location of the calibre folders on my other laptop once I get it back and I guess the desktop shortcut will have to be updated as well.
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