I'm curious as to someone who has a collection of thousands of records actually knows what they have and how they decide what to listen to.
About 10 years ago I decided to make the switch to digital and started converting my LP and open reel collection. That was about 2,000 albums at the time.
In the process, I discovered a lot of material that, 1) I'd either forgotten I had, or 2) I couldn't even remember acquiring. (There were only a couple in that category.) Discovering I had copies of a few un-released masters on open reel was a real treat.
One advantage of a music server is it makes searching your collection much easier than checking what's on the shelf. Doesn't matter if you're looking by album, song title, artist, year, genre or whatever, I just find it a lot easier to enjoy what I have.