dnalbach said:

  Thanks guys for all the info and insight. 
 
Unfortunately, there was a home theater accident this weekend that necessitated buying a new receiver. Ironically, it was my fault, not the wife or kids. Always check cable slack before moving anything! What an idiot I can be at times. Anyway, replacing the receiver set me back quite a bit more than my headphone budget, so headphone stuff will be on hold for awhile.  
 
On the plus side I can use the wait time to develop more of a long term plan. With all the great discussion here, I'll be able to reference this thread for a long time to come in my planning.
 
Regards,
Daniel

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Oh man I'm sorry to hear that :[
 
It's accidents like that, that usually lead us [or lead my self] to wind up getting something like teh Fiio E17 or E07k as a temporary step up, At least until you can save enough to get a nice step up again. THere's noting wrong with going with a tempoary solution like the E07k or E17, gives you time to carefully plan for a bigger step up in teh future! Plus you can re sell that E07k or E17 here on head fi for about 75-90% of what you paid for it. 

I moved the old receiver that I just replaced into my office and connected it to my desktop. It's a Yamaha RX-V995 and the headphone jack works fine.
 
A headphone amp may be unnecessary for awhile with this setup, and portability isn't much of a factor for me currently. I can already hear a minor difference in sound, mostly in the clarity of the sound across volumes. In fact it seems like I can listen to a higher volume without fatigue using the receiver, with more balance across the tonal range, so that's interesting. 
 
The sound card and it's line out port are clearly a weak point though. Now a standalone DAC looks intriguing. The Schiit Modi might be possible, and I could just manually move the USB connection back and forth between the desktop and laptop for now. What's a few more drops of blood when you're already hemorrhaging, right?
 
[edit]
 
I just connected the receiver to the Macbook Pro's line out jack and the difference surprised me. Should have thought to try that at the beginning of this thread. My desktop's integrated sound card DAC and components must be significantly cheaper/crappier than what they use in the Macbook Pro. Obviously the MBP isn't audiophile quality either, so I guess there's still a lot more room for improvement. Very interesting. 

@dnalbach, if you are interested in some more inexpensive portable usb DACs, here is a list of sub$200 dacs & their chip: http://www.head-fi.org/t/696401/giant-list-of-sub-200-portable-dacs-w-their-chips-price

money4me247 said:

  @dnalbach, if you are interested in some more inexpensive portable usb DACs, here is a list of sub$200 dacs & their chip: http://www.head-fi.org/t/696401/giant-list-of-sub-200-portable-dacs-w-their-chips-price

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Oh nice link man! I may check that out ym self  

That's a really interesting list. Is there any quick and easy way to tell which DAC chips are better than others?

dnalbach said:

  That's a really interesting list. Is there any quick and easy way to tell which DAC chips are better than others?

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unfortunately no. i've even heard of some manufactors not sticking with the higher number being better, while other manufactors do. it's hard to directly compare chips from different manufactors as sometimes good chips can be implemented badly or whatever. the best way to figure out what to get would be to find comparison reviews against the highly rated products.