In some cases a good pressing of an LP will sound better than a CD or CD-quality file in my system. I have some digitally-recorded jazz LPs that sound better than their CD counterparts, even. But in some cases a CD sounds better than even an analog LP.
In general, I find a digital recording needs to be at least 96kHz sampling rate to equal the SQ of an LP. Admittedly, my current digital front end was less costly than my turntable, but it sounds better than earlier digital gear that was as pricey as the turntable/tonearm/cartridge. I think digital gear has advanced enough that you don't need to spend as much on it as in the 1980s-1990s. But maybe the most expensive digital gear can make a worthwhile improvement in the SQ of even CDs.
For playlists, the old analog method was mix tapes, preferably made on tape decks that were tuned to the specific blank tapes used. Such recordings can be nearly indistinguishable from their sources in many cases, and if you played them on an auto-reverse deck you could get 90 minutes or more of continuous, all-analog music. Cassette tapes I made in the 1980s still play on my Nakamichi decks, and those decks have rarely damaged a cassette--when they did it was because the transport system needed repair. Reel-to-reel can provide even better SQ if you have the space for the deck and the tapes.