music file storage/playback suggestions please

I've been backing up my music files onto a hard drive for archival purposes, but have recently started using my computer to listen to music through a DAC. it's easy enough for LP files (there's just side 1 + side 2, i.e. I only have to click twice), but I'm thinking of putting my CDs onto the hard drive now, but it'd be a pain to have to click for each track. I know there are programs/apps for this, but I'm hoping to skip all the research, just get recommendations for a program/app that people like - and hopefully isn't too pricey. thanks!
creating an instant playlist is great on the fly if you do not want to listen to the entire CD when you select it from the 'Play Now' list. I use JRiver and iTunes.
foobar2000 open source if Windows but you'll get better sound from a streamer. Most have player apps that you can play folders, genres or make playlists.
I use Itunes on the Mac.  I created "Smart Playlists" by genres (for instance: "Match music for the following rule: Genre is Rock").  After that it displays much nicer - a whole page of thumbnails of CDs.  Much easier to use.  The only drawback is that it doesn't "see" other genres, so anything that is "Rock & Pop" has to be edited/changed into existing genres - Rock (or Pop).  The other limitation of Itunes is inability to play FLAC or to play anything above 16/44.1  It's OK with me since I only rip CDs and use ALAC (Apple equivalent of FLAC).   
Here's another alternative -- I use Logitech Media Server (LMS) to manage and play my collection of 60,000 saved music files and also Qobuz. LMS will play through a software player on your PC (Squeezelite) and also supports a variety of separate standalone players -- I use Raspberry Pis configured as players. One can also buy the original Squeezebox players on the used market, but the RPi options are better.

LMS also supports multiple players and that be synced if you want multi-room playback. Both LMS and Sqeezelite are free downloads.

Hello MUsicSlug,

 I do not have a solution for your question, but a question myself. May I ask for your expertise and guidance? ow can I connect my music collection on a FLAC USB to my pre-amp listed here? My sound system is an early 80s ‘stack’ system.

None of the components are digital: Bryston 2B solid state amp, Conrad-Johnson PV-11 pre-amp, MIT 330 interconnects, MusicWave phase-equalized speaker cables, California Audio Labs CD Alpha and Delta drive, Dual 1129 turntable. B&W 803 speakers.

I would appreciate your suggestions and guidance on the matter.Thank you.

Mark Saracino

hi Mark - sorry I didn't see this until today. if I understand right, you need 2 things: a computer to send the files, and (optional) a DAC to convert the files to analog so your preamp will play them. most computers have decent DACs these days, so whether or not you buy an external DAC depends on what quality of sound you're after. in other words, plug the USB thumb drive (I'm assuming that's what you means by 'FLAC USB') into your computer; the drive will show up on your desktop, so you can click on that icon and see all the files; clicking on a file should automatically start it playing. I'm a Mac user, so I have itunes, which I like, but I'm sure there are lots of options for how you organize your music if you even want to. if you end up not getting a DAC, you'll use the headphone output on the computer (with an adaptor) to go directly to your pre. hope that helps.