From Mac to PSP-What's the BEST method?

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Hello,

So I just bought an old PSP from my brother for $40. Which isn't a bad price, I mean it's pretty beat up.

Anyway, I just picked up a 4GB memory stick ($24.98 from eBay)
and i'm wondering what's the most efficient method for transferring music, pictures, and videos to the PSP.
I at least want all my music on it since my iPod Mini died, which is 2.24GB off the playlist of songs I actually listen to.
I have the pics from my S5, but I don't need to put a lot on, if any really.
I have some videos, some from my S5, stuff like that. Some .VOBs too.
Converting?
I'm sure this 4GB is gonna go quick, but what's the most common method? I could just hook up/drag/drop I think, but is there any special software y'all use?



Oh, and what about replacement housings? I need a new front, well I could live with just the new analog stick, the one I have on now is aftermarket and huge and makes it stick.
 

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