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I'm 53 years old and started buying CD's in 1987. I get where you are coming from. But...
Honestly, ripping a ton of CD's is not a big deal.
20 years ago when I decided to go all digital I had a cd collection over 500 discs. Ripping them was my winter project. While watching a hockey or football game, at every commercial break insert a new disc to rip. It's not like you have to sit in front of the computer while it's working. At a rate of 20 discs a day it goes pretty quick and a month later you are done. And you'll be glad you did it.
Aside from creating a number of different play lists based on genre or whatever, I created one that is simply every song I like. That list is currently 1700 songs. I normally just select that list and set it to shuffle.
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