How do i use 2 i pods w/ one i tunes library ?

i have a first gen. (fire wire connection) i pod that i have used sucessfully for many yrs.i bought a nano for my wife, installed the software and have been sucessfully loading it w/ music. now when i hookup my i pod, it says do not disconnect and the computer apparently dosent recognize it- the "roberts ipod" does not appear in the margin. note: when i set up the nano (with the help of appple phone support) i did so under the same user account as mine was on and do recall uninstalling something. do i need to reinstall the software for my i pod ? if so, does it have to be under
a different user account ?

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How do i use 2 i pods w/ one i tunes library ?

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