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Manage music manually will not stay on in iTunes

Hi,

I am using latest version of iTunes and on a PC. When I check manually manage music it does not stay checked the next time I open iTunes and go to sync my devices.

I read that since I drag and drop I am supposed to have that on, but to be honest I don't even know what it actually means.

So, my two questions are-
1. Why does it not stay checked?
2. What does having it on actually mean?
(Whether on or off, I have no problem dragging music over to my devices).

Thank you