Sony Walkman S series, anyone?

Wanted to get the older generation iPod Nano for one of my kids, but apparently not many places still have them. Folks at Best Buy said that the Walkman was directly compatible. I had no trouble transferring iTunes music to the unit, but video seems to be a no-go. I did the online tech support chat, and was told that I would need "any third party converter" to reduce file resolution to 324x240, or something like that. I found one that would do it, but it keeps saying that it does not support the format after it does the conversion.

Does anyone know of a different program that I should try, or, ultimately, a source of the previous generation Nano that supports video?

Why the hell is this stuff always such a pain in the ass?

amazon is your friend