Alright, I did this and it did give an error that I'm really not happy with. It said that the path is too long and must be under 89 characters. I never had this issue running from my laptop, but all of my backed up/synced files are in a folder on the external hard drive making the path longer. I'd be willing to shorten the top level folder since the path isn't that much over(92 characters), but changing it would cause a bunch of issue for other things.
My other copy of Calibre Portable has path name that's just under the limit, and that will let me manually select the library, but it still won't let me run the calibre-portable.exe file after doing that, so I'm not sure exceeding the path limit is the reason why that file won't run.
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