I also enjoy music on all kinds of formats and systems. In my bedroom I have an old Tivoli radio/receiver with a CD player (very inexpensive), small subwoover, and extra speaker for stereo. It is about as inexpensive as a system gets. I often listen to classical radio on it. I like being surprised with composers and artists I haven't heard about. I also listen to the radio in my car. I like music. I listen however I can get it. But there is nothing quite like a good vinyl recording.
On my main system, I have a pair of headphones. My Sonus Faber Olympica Nova V speakers have three 7" woofers that pound through the wall. When my wife is home and I want to listen to something loud, I move over to headphones with a fairly modest headphone amp.
In regards to upgrading my digital system to be as good as my analogue system, well, I think that might be a complicated story. First, as much as digital folks can say that my streamer is not up to snuff, I like it and recognize it's not the best. As I have said before, it errs in a way I like, softening the music. Since digital music tends to be hard at times, I don't at all mind my Moon 280D's shortcomings. If I ran into some money, I would buy a new streamer. But getting it to the level of my audio chain?
Let me just say this. In an Absolute Sound review of dCS's new $250,000 DAC. Michael Fraemer, the analogue expert, praised the new DAC with these words. "It's almost as good as analogue." $250K almost, let me repeat almost, up to analogue. I'm not spending 1/4 of a million dollars to come close to analogue. But, yes, I could upgrade my digital setup if I ran into money, but it won't be at the level of analogue or even close on my budget.
But once again, I listen to music in many ways, and enjoy it no matter what form it comes in. I just like analogue better. Just like I like digital music at 192 kHz with a 24 bit word length more than 44.1 kHz at a 16 bit word length. But if what I want to listen to only comes in a 44.1 format, I'll listen and enjoy the music. I listened to Beth Orton's "Central Reservation" at 44.1 kHz yesterday and loved it.

