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Not sure which software you are using to rip, but you can use itunes as a ripping tool for use with any .mp3 player.
Make sure your settings are decent. If not, start over.
You can definitely hear the difference between big files and small files. Maybe not with headphones, but very noticeable if you plug into a decent system.
I use 320kbps Variable Rate Bit encoding at 44.100KHz.
You can get away with 256kbps but with memory as cheap as it is these days, why bother.
If you want to get serious about ripping, then Exact Audio Copy is the benchmark for quality.
It's free and will produce perfect rips.
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Randy
'87 911 Targa
'17 Macan GTS
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