Dave, your setup sounds much nicer than mine! I just run an output from my receiver to a laptop with Audacity installed -- it works just like recording from a record to a cassette tape, but your computer is the location the music goes to.

Organizing it and playing it is another problem.

For years I've been talking about getting a dedicated desktop/laptop etc to use for music since it's gradually been taking up more and more memory on my computer (currently about 110 GB with just under 10,000 files, but still growing). I find it easy to set a record/cassette on, go and do a chore for 15-20 minutes and come back to flip it over or start a new recording.

I originally organized my music in lots of folders, split up by artist and album and had each song split as individual tracks like that. As the size of the folders grew, Windows Media Player had more and more "cache" issues and would frequently mix up album art, take a while in recognizing newly added tracks, etc.

Now, I keep (almost) all of my digitized audio in one large folder and use a program called Clementine to listen to it. It's a neat music player that can be powerful to use, but it does take some getting used to when compared to more straightforward music players (mainly WMP). The main benefits include "smart" playlists (where you can make the playlist automatically add new songs that meet certain specified criteria) and that it's good about properly reading files, even large amounts.

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For all the doubters -- converting your music is worthwhile. While it may not be as high a quality as the original (depending on what file you use) I find the convenience of being able to listen to obscure songs I can't listen to on YouTube, Spotify, etc. With that being said, I'll advise that you should only convert if it's worth the hassle: if the record/cassette you're holding is already (readily) available on the internet, don't bother -- save 30+ minutes and convert another one.