If you had to start all over again in this day and age

I would do everything exactly the same. Never regret, never apologize. 
Acquired 500 records in the 70s which are some of the best I have. Went through all the formats. Back to vinyl but still listen to CDs, digital, streaming. 
Loved the journey of trying to figure out how to acquire next component and what sound I like, which has changed from decade to decade. 

“I'm a chicken to move toward streaming. It took me years to get a cd player. To me an audio system is still about a tt, a player and a good ole single ended.“

I was there not long ago. During this pandemic I wanted a project so I ordered a hifiberry dac plus DSP $70 and a Raspberry Pi 4 $60. Another $10 for a heat sink case, a few bucks to download Volumio, and you are in business. Initially I attempted to build a Squeezebox type of thing with a screen, but realized this was overkill. I took an old iPhone and use it with Volumio app as my front end.  So far, the ease of selecting a wide variety of music and HD downloads points towards success. I had some help from kind folks on here to get through the software portion, but if I had just read thoroughly that could have been minimized. It doesn’t have a $400 glitzy case or front panel with pretty lights, but you won’t regret the $140 cash outlay, and the whole unit can hide in a small part of your rack. Don’t over complicate this as I did. Simple is good. If you need help, let me know. 

Thanks ovine. Although my knowledge of traditional equipment and its innards and tech has done me and my customers well throughout the years, I know next to nothing of this new digital stuff.
I understood "dac" and "case" in your post but I have no clue what a Pi 4 is nor "volumio" or where to download it on.

You know what is really putting me off on this streaming stuff? I can’t own the music. My tastes in music run rather tight. I am NOT an "overall" music lover by any means. "Hip-Hop" or "Rap" will never see the inside of this house ( except for one very hauntingly beautiful rap I heard as a prelude to a Blue Man Group show) as well as Michael Bolton or Barry Manilow or Janis Joplin or Kenny G and God forbid, Alanis Morrisette.

I have bought entire albums for just one song. There are only a few classical reproductions I like. In short, I’m rather "selective" with most of my preference in note structure associated with minor cord grouping.

It makes me wonder if this whole streaming thing is right for a person such as myself as opposed to finding a song, buying it for $1.99, burning it on a cd and playing it on what I consider a very good player.

That's fair - that "ownership" versus "renting" aspect is a hurdle for some.  If you're happy enough without the streaming then just keep on with what you're doing.  Surely not for everyone.

Wireless streaming of FLAC and Amazon Music HD (which I've already done). There's no difference between streaming and a CD ... except convenience and having a massive library at hand. Bits is bits.

And I would have stopped creeping up the upgraditis speaker ladder and just gone straight to the top of my wishlist. It would have been cheaper.