I'm not certain, but you might be able to make an iPod Classic talk to an iPad (you might also be able to do it with a raspberry pi + Linux + iTunes running in wine). If it does work, there's the catch that you'd have to convert your files to aac (also known as m4a, lossy and similar to mp3) or alac (lossless and similar to flac).
If you try an iPod and rip CDs or convert from flac/wav, make sure you convert directly to your desired iPod-compatible format, avoid converting from mp3->aac unless you don't have the original lossless rip. Doing so is like repeatedly opening and saving a jpg. Each time you do it, you lose some quality.