Can you transfer files over network connection
No, pre-touch iPods don't have any networking, they need to be plugged in to transfer files. This iPod is still going strong! I considered getting a bigger SD card for it since my library is now bigger than 128GB; but I've just been more selective about what I put on it and that's been a good plan too!
I'm kinda picky about sound-quality on things and I from my testing, aesthetics aside, the iPod sounds better than the iPhone 4, and the iPhone 4 sounds better than an iPhone SE (the last one with a headphone jack) - I think over time they were de-emphasizing sound quality on the headphone jack. (based on this, if anyone is considering an iPod Touch, I think the 4th gen would be better for music than the newer ones

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