I remember back in the 80's, when I first started working as a host, the general feeling was that there would never be a need for more than a couple of thousand songs in a collection because someone could always find something they would like to sing in that songbook!
When I finally went digital I was carrying around over 5,000 discs in gator cases (I never got used to those flip folder types, the fastners kept giving way!), and it was a hell of a time to rip all those discs, especially, as you say, the annying protections that producers put on their discs. I used to especially despise Sound Choice, who, as you mentioned really made it difficult to get to the last track on a disk...
I had a bank of different Plextors, and a dedicated PC system (sort of based on the EK custom disc pc's you could find in many Karaoke shops of the time) because I found that some of the earlier Plextors coped with some disks better than the later ones. (Who remembers putting Adaptec SCSI boards in their PC's?)
I even invested in a wax thermal transfer printer to label my working discs (I learned very early on that it was not wise to work with the originals - after having a flip case break on me damaging a whole load of Legends disks dropping edge on onto a cobbled street! - even though it was a risk to do so if caught out!
As you also point out, having a well configured USB 'Windows To Go' stick, and a backup of your Karaoke Library and Main music tracks on a large backup SSD gives you far more lattitude in the event of a laptop failure unless you are a belt and braces guy like me who carts around 3 identically configured 17" laptops with registered copies of working software on each (You ever tried to de-register a copy of Karma from a failed PC and register the software on another when you are in a location with no wifi and lousy cell reception?) and 10TB of SSD storage in each for my Karaoke, Music and Videos!