iPod Problem with IPOD video switch to mac

[araBRUNO]

Okay I had all my music on my PC desktop for about a year and half now. My 5g Video iPOD was formated for a windows machine. I just bought a MacBook Pro and copied all my music to my MacBook Pro and formated it for Macintosh. Which included the restore the factory defaults.

Every time I plug it in a nice friendly message pops up and says iTunes cannot copy my videos because my ipod cant play them...

if i just click okay it tries to synch up the computer with music etc. Then about 1/4 into the way i get "The iPOD "araBRUNO" cannot be updated. An unkown error occurred (-50).

I don't know, if it was a PC problem I could just hit something hard enough and it usually fixed the problem, but as far as going into the Mac crap of everything I am baffled and amazed at all the new guey interfaces and "help" hints.. Please tell me what an idiot I am and tell me how to fix it.

 

[pianoman]

perhaps the 5 Rs could be helpful here... particularly restoring the iPod.

also, is your new computer authorized to play any songs you downloaded from the iTunes Store? this might clear up the issue of not being able to load the songs because you can't play them.

maybe someone else has another suggestion for what the problem could be and how to fix it.