Is there a way to play/convert large FLAC libraries on Ipod Classic, without having to pre-convert each of the folders?

Question

Hello,
I'm looking to get an Ipod Classic due to the huge memory it has. The majority of my library is in FLAC and made up of full albums, some with cue files as well. My library is well over 2TB (external hard drive) and mainly FLAC with occasional MP3s and WAV. I'm looking to transfer a bunch of albums in 16/44.1 FLAC on to Ipod Classic. I looked into Rockbox as I did with Sansa Fuze, but as of right now, the Ipod Classic isn't listed. I really wish there was a native way of playing FLAC on the IPod Classic.
So the next best thing I could hope for is to convert FLAC to another format (ALAC or WAV...maybe MP3 for more space, but really want to stick with lossless). Is there a way to queue a bunch of albums (folders) at the same time and have them converted into another format suitable for playback on Ipod Classic. Regarding this conversion process, I have two aspects I am looking to achieve.
1) The conversion process should be on the fly. I really, really don't want to convert all the FLAC to another IPod format and then keep those converted files on my hard drive until they are transferred to the Ipod. I would much rather prefer something that could extract my FLAC folders from my external hard drive, process, convert, and transfer to the Ipod directly, without having to keep anything directly on my Macbook. This is so I don't run out of space. Also, it's much more easier that way. I don't care much about the time in this process as long as I don't have to constantly doing things manually. I would like to maybe move, say 40-50 GB at a time, until I max out the 160 GB 
2) Proper catalouging of the converted files - I don't want the files losing all their tagging information and coming up randomly, disorganized on the IPod. I understand ALAC is better at this as it can retain the data while WAV can't, but I would still like some input as I have never tried ALAC before.
I looked at MediaMonkey, although I'm not too sure about it. Also, I have a Macbook Pro Retina, so a native app would be the best.

Answer 1

You cannot put music onto your iPod without using iTunes, that what iTunes is for.
It's also not a good idea to wipe the music from your computer and having it only on your iPod. We see countless posts here from people who have done just that - and then lost everything when the iPod needs a Restore. Even if you never need to Restore your iPod, what happens when you eventually replace the iPod? You'll be back here asking how to get the music from one iPod to another. That's not easy to do, we see countless posts about that too!
A much better idea is to buy an external drive (a proper external drive, not simply an iPod) and put your large amount of music onto that drive. Then point your iTunes Library to that drive. However, you need to remember two things:
You still need a backup of that Library.
Using an external drive as your iTunes Library means that the drive must be connected and ready to read before starting your iTunes programme. If it isn't, then iTunes will look on the C: drive - and you will find no music in your Library. (Once again, lots of posts about that as well!)