Pink Floyd and Weed

Room’s own website is excellent - Roon is not like any other service so it is a must read. 
But basically, you install software on a powerful processor (like your home PC or Mac). You then install Roon apps on your phone or tablet which you will have with you in your listening room, to control the music. 
Then you connect suitable streamers wherever you want music; as many as you like - I use a Bluesound Node, a R-Pi, a Chromecast, other Macs. If you want you can also connect a DAC directly to your main processor. 
Roon finds each streamer/DAC and can send different music or the same music to any combination of them. Each end point can have a custom profile of DSP and other filters. So for example if you only use headphones with your Chromecast you can build in a DSP profile for that combination. 
You hook up Roon to your NAS, to Dropbox, to your music folders on your main processor, and to Qobuz/Tidal.  Roon finds, sorts, and describes what you have got, dragging in information about the music it finds and showing it to you on your controller devices as you listen. It’s like having the best LP covers of all time, for all LPs, instantly. 
Best of all is the audio metadata. Roon tells you loads about your signal path quality. It is a digital fiddler’s dream.  

@grm  First are we talking problems with Division Bell or everything through the headphones?  Accepting that this is a general problem not DB specific, do you have any way beside USB to get out from your computer?  I live in Canada so I am too busy rolling to spend much time swapping from USB to co-ax or toslink to compare sound.  I use something completely different to get hi-def and vinyl transfers from my PC to the stereo so I never bother with it but I have seem many posts commenting on differences between the various methods and USB didn't seem to be very popular.  Great for compressed or low def formats but the better the audio signal the bigger the differences according to most who commented.

As for the other issue, have you watched the Gilmour in Pompeii blu-ray?  Great show and if you take the same break the the band takes between sets ;) the startup to the second set will blow you away, crank it!

bluemoodriver,
Thank you for the detailed description of Roon, sounds like a nice enhancement to the overall listening experience, I will check into it!

russashe,
Found David Gilmour Live at Pompeii on Spotify, listening to it now, what a blast, thanks for the recommendation! Listening to Spotify, I eliminate the USB cable and go strait from my network via a Cat7 cable directly into my streamer from my gateway. In the Spotify App, it shows all of the devices on my network and I just select my streamer and I'm off to the races.

Back to headphones. I found there to be similar results with respect to the overall lack of the bass registers. I connected my HD600's to the headphone output of my SACD player and my HT system, in all cases the bottom end seemed to be truncated, across all devices. However, even with the lack of bass, the HD600's sound great.

Back to the concert! 

@grm Are you hearing weakened bass through the headphones on other sources or just the streamer.  If it's everywhere is there a chance the headphones are wired out of phase?  
Just as an experiment, use the equalizer in J-River to wind up the lowest two faders.  If you get the expected bump in bass energy see if there is a boost setting that makes the phones sound more like you want.  Also run the faders to the bottom to see the effect.  Try the same thing with your speakers, of course watch your levels, massive boost at low levels can be dangerous.  Also check out the analyzer in J-Rivers DSP section.  The graph will give you a decent view of the music you are sending out.  It's great fun to watch if you are a music lover who is also a tech head.  After you get used to looking at it you can easily see if a track should sound bottom heavy, balanced or bright.  Being able to see the "tone profile" of a track makes it easy to determine what the overall sonic character of the song is.  Before I get jumped, no it's not a high precision evaluation technique but it does help.

russashe,
The HD600's are wired correctly, the connectors on them are keyed in a way, one large and one small pin on each connector, you would have to use quite a bit of force to wire them out of phase.
I have fumbled a bit with J-River and am concerned I'll mess things up if I am not careful. I am using Media Center 23. It sounds like you have a more in-depth understanding of J-River. Any way you could share something like a fault tree that can get me to these settings? Anyone out there with J-River that might be able to help? Thanks!