If you had $2000 to upgrade this system...

Kbark- Not offended. Thanks for the input. Right now, I really only use the V-dac&link for streaming Pandora generally as background music while doing something else (e.g. cleaning vinyl). If I ever get serious about computer audio or decide to upgrade CD playback -maybe that is when to invest in a much better DAC. Use Denon as transport or get something else. Will keep your comment about Rega in mind.

I agree with the above posters re: the digital front end, IF you listen a lot to digital sources. No experience on the TT or phono stage (though Black Cube has decent reviews it seems). At under $1k, maybe something like the Rega DAC, a MiniMax DAC? Above $1k, I'd look at Wyred4Sound or Antelope Zodiac.

I also think a sub might help out here if you are listening to music that could benefit from a bit more in the bottom end. Big fan of REL subs. Integrate very nicely with speakers using the speaker level connector.

I would also recommend looking into a power conditioner upgrade. I love my Running Springs Haley, but there are also great products from Shunyata and others. Power conditioners are very system dependent IME, so try a couple out in your system if possible. But most of the big names will be a significant improvement over APC.

So at the low end of what you mentioned, I'd try to upgrade those three things.

At the $5k end of things, I'd start thinking about new speakers or taking a big jump up in terms of your most-used/most-valued source. Maybe a table like a Well Tempered Amadeus (which I own and love) or Simplex? And if vinyl is a priority, check out the Jasmine phono stage. Folks seem to love it. The Dynavector P75 is another phono stage I have liked (for MM and now especially in PE mode with a low impedance LOMC).

Thanks to all for your generous giving of time and ideas. Feedback has definitely helped me understand how I would structure upgrades. I'm thinking analog first (phono stage right now), speakers next (subs because I do love the Forests), digital last (things really sound great even now). I guess it's an iterative process. Totally new CDP or transport/DAC would be easiest (lowest risk from my perspective). Totally new speakers (higher efficiency but still 2 way??) or new TT/cart seem more prone to buyer's remorse. These would be further down the road if ever.

Funny - when I first started posting on A'gon I thought I knew something about audio. I certainly had (and still have) a lot to learn. Thanks for all the help in my education.

Funny how we all forget about the room.
I could only imagine how different the same gear would sound in
say an:
livingroom
basement suite
basement suite with cement walls
above with carpeted floors
hardwood floors ect.
As Alan Parsons said,pro audio guys prioritize the room,where the HiFi world prioritizes the gear,brand names.
I had done the same,gear first,components cables ect.
For me the hugest difference was treating the room,starting with basstraps in the corners really tightened up the bottom end thus cleaning up everything above.
I believe Two grand in room acoustics would make a major change for the better than any component,cable ect.

Just something else to think about as I've been down that road over and over again.
The room is so big compared to our gear that we can't see it
even though it's bigger than anything else.
Kinda like wearing horse blinders,we just see or hear what's in front of us and not around us.

good luck on the hunt.

Drummer - Thanks for your input but really haven't forgotten the room. Have spent a lot of time experimenting with speaker placement trying to optimize in an admittedly not ideal room. Also, see comments to Mapman. Will likely get more serious about "store bought" acoustic treatment if/when I move into a larger listening area. Am hoping to incorporate acoustic prep during the actual rennovation of that space.