FLAC is a lossless music format, not really supported by Apple. Apple used their own format called ALAC that is also lossless.
iTunes only supports ALAC, just like iPods and iOS does.
iOS (not iPods) may have started to support FLAC with iOS 11.
Both formats range from 16 bit at 44.1 khz & 96 khz, 20 bits @ 44.1 (HDHC) & 96khz, all the way to 24 bits @ 196 khz, (SACD, DVD audio & Blu-Ray)
Your source media has to be very high quality to get the benefits of the higher bits.
Hopefully you have the space on the computer to make all your music lossless. The file sizes are huge (325 MB for a whole CD, around 18-20MB per song). About half the size of the CD as raw data (650MB).
If making them lossless is what you want, then sure, you can do that, but if you are using the headphone jack, it isn't worth it. I wouldn't because my music listening is limited to scenarios where I would not be able to discern the difference in quality of a lossy (MP3, M4a) or lossless track. Maybe if I were running iPod audio out the bottom port to my sound system directly I could tell the difference. I typically play my audio through the headphone jack or Bluetooth (iPhone) and those connections make it so you can't tell the difference between a high quality rip and lossless.
iPod can't play FLAC files, they must be ALAC files using Apple's firmware.
Rockbox can play FLAC.
Wavpack is interesting. It basically creates 2 files, one is lossy (compressed about 60% of the original size) and a correction file that together recreates the music in lossless format.
Rockbox plays the lossy Wavepack file without applying the correction file (at least in 2009) in an iPod, so you may be good enough with MP3.
I am also seeing issues with higher bitrate files on the iPod with Rockbox, and recommendations to limit it to 44.1khz with either 16 or 24 bits. Higher bit rate files may skip.
ReplayGain can handle FLAC files, no mention of wavpack files though.
WVGAIN is a utility that comes with Wavpack and it can do this.
It really depends on how much you want to invest and learn. This is well outside of my expertise. And since it is getting away from Apple, getting off topic for this site.
I personally would just use high quality lossy rips (256 AAC) because I use headphones or Bluetooth and both are bad at real reproduction.