I'm at a digital loss or getting over UI mountain

It sounds like you are a victim of Apple when all you need is a decent tag program like mp3tag.

No you don't need (often for the better) a computer to listen to music.

I would like to propose that streaming has fundamentally changed music for the audiophile. It has been a complete paradigm shift. Ownership points you to a very limited library, and being confined to that library. My ownership is 4,000 albums. Something you could kind of keep in your head. Streaming opens you up to about one million albums. With a good streamer, depending on the rest of your system, the streamer can have higher quality than your CDs, stored files, or vinyl.

You can make the transition into a new Paradym with an old way of looking things. Then over time you are likely to discover that this is a different world. When you have basically access to all music, things change from locating the same old stuff to exploration. My habits completely changed over the first couple years of streaming once the sound quality was equal or better than CDs and vinyl.

So, first, I recommend putting a lot of effort into getting a very high quality streamer. Personally I prefer Aurrender at about any price point. I would not worry about taking your old files along and organizing them. Sure, throw them onto your streamer in case you lose your internet.

The Roon question is a good one. Great quality streamers have exploration and library tools. They will combine the stuff you own with stuff you find in streaming. Roon is a good exploration tool, but it is a hassle, cost money, may degrade the sound, and is really unnecessary. The functions provided with Aurrender are really adequate to help you navigate, explore, and collect new music (leave breadcrumbs to find what you liked).

If your personality is very anal retentive then a streamer that supports Roon is the way to go. But not a PC or MAC… a real high quality dedicated streamer.

My recommendation is to work on getting a world class streamer for your system… focusing on sound quality… then learn what the world of streaming is like.

I now primarily listen to music I have never heard before instead of the stuff I bought… everything I bought is already there. Sometimes I’ll locate an album I used to listen all the time and listen to earlier and later recordings by the group or adjacent groups. It is a truely incredible works of music and opportunity to explore.

Oh yes, you want to use the Qobuz service. Sound the best and the have over half a million high resolution albums… and that is growing every day… and for the cost of buying a new CD each month… what a deal!

Good words concerning the paradigm shift. I will heed these.

You can give Roon a shot with free intro subscription no cost. It should be able to get you to a much better streaming place. It’s one of my best hifi investments in recent years. Just make sure to run the server on a suitable powered platform. 

+1 @ghdprentice

To speak personally, I have decided to stop worry about managing files -- DVD’s, CD’s, etc. It’s not worth the time -- to me. Streaming is reliable, Roon is an amazing organizing tool, and even without Roon, playlists on Apple, etc. are simple to use.

It’s all data -- data on vinyl, data on CD’s, data on streaming services. I would rather discover new music, compare renditions of pieces I know well, or return to old favorites in a playlist -- e.g., called, "My Music" for the CD’s I own but am now streaming -- than spend time shuffling things around in files. Life’s too short, for me.

I agree with others that the music collection concept is fading with the availability of high quality streaming services for a monthly pittance. Look for a good dedicated streamer that has an interface touted by the folks in this forum. Aurender, Innuos and Roon are all high rated for their UI’s. I just implemented Roon on a low cost “renewed” Mac Mini running Ubuntu, easy enough, but I worked as a software engineer for thirty five years. If you don’t like to mess with tech, find the best streamer with a native solution and get a Qobuz account. 

Good points by members here about Roon, which seems to take occasional hits related to sound quality but most find it acceptable especially given the access to informative write-ups about artists, the many music choices available through Roon's administration of TIDAL and Qobuz all from one platform, and Roon Radio, which serves as sort of an AI-type musical source that plays selections based on your previously played preferences.

On the downside, the costs do add up, but maybe compare to other costs we have accepted as the norm in our expanding digital world, for things like our phones, internet, and cable/streaming television.   I purchased Roon Lifetime (originally $500) early on , which ended up being a good move for me, and I also have monthly subscriptions to both TIDAL ($10 or $19 if you use MQA) and Qobuz ($13).  Currently Roon is $15/mo or $12.5/mo if paid annually, or $830 lifetime.  You could contrast those costs against purchasing physical media, which I rarely do any more.

In my opinion, the UI and UX Roon offers are simply unbeatable. But to get the best sound quality from Roon you will most likely need either a solid, fanless roon core with a good streamer (Lumin seems to work well in this configuration) or the top tier Roon Nucleus + used as both the Roon Core and a streamer. Another option is something along the lines of Grimm MU1, which is both the Roon Core and a streamer that comes at s much higher price.
There are ways to make Roon sound good. However, there are streamers that sound best with their proprietary UI. Auralic is Roon ready but my experience is that you get the best sound from its OS/UI and not using it as a Roon end point.

I understand why folks like Roon. I have tried it.

For the last forty years I have been early adopter of hundreds of software products, for personal computing, groups, and global enterprises. The one thing that you can be certain of is that today’s specialty niche software will be gone tomorrow. I can’t off hand think of a single program I used in the 1980’s that is still in use… Lotus 123, Word Perfect, DOS… photo processing, browsers. Niche stuff has much smaller life cycles. Either the functions will be included in other companies devices, or company will get purchased and included in someone’s devices, or the product and company will whither away and disappear.

Its time is probably limited. If you love it, use it. But I’d think hard about buying a lifetime license.

This one hits hard for me. I'll probably buy a purpose built streamer of good repute and see how it goes.