Imo, upgrading is a logical step. There are good amps for the Sennhs on the market. How much are you willing to spend?
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I would recommend a Woo 2 or a Decware CSP-2 as an upgrade, or a Schit Valhalla if you want something cheap. Both will make Sennheisers sing. I would avoid solid state.
I don't know much about the ASL headphone amps...but they never gathered much of a following on Head-fi, a sign that you can do better for the same or less money.
I think a good solid state amp with your headphones sound good. I think finding a Gilmore Lite is an excellent amp. If you must go tubes then the Little Dot MKIII does a terrific job. Subjectively I prefer the Gilmore Lite but the LDMKIII is hardly a slouch. Plus you can tube roll if that's your choice.
You might want to bring your question over to Head-Fi.org, if you can tolerate the signal/noise ratio of the posts there. There's a whole bunch of great headphone amps that would work well with the 580 as they're not that difficult to drive. It really depends on your budget and expectations/goals. I recently heard Schiit's new Lyr amp with a few different cans and was very impressed. You might also consider upgrading the headphones if headphone listening becomes a priority. There are many options that sound significantly better than 580's to my ears, but certainly always at some significant cost increase. For the $ they are a very good headphone.
Thanks to all. S/N too low at headfi. The music she doesn't appreciate is the loudspeakers, thus, the idea of a move to cans. I like all of the ideas so far. I know that listening is the real solution, so I will buy the most likely candidate and sell it if it doesn't work. I also know I can't generalize about SS vs tubes. I'll keep the 580s for now. Great ideas. I'm open to all suggestions except different cans.
I agree that Head-fi has deteriorated in recent years to the point that it is impenetrable unless you keep track of members who have something of value to say and ignore those who are just running up their post count.
FYI, I have owned a lot of headphone amps in the last six years, including amps from Luxman, Meier, Woo, Singlepower, Blue Circle, and Original. I have also attended meets and have heard amps from Ray Samuels, Burson, TTVJ, and Decware.
Headphones like Sennheisers have a fairly high impedance. I have found that OTL headphone amps offer the best sound quality. If you like Sennheisers and can afford an OTL from Woo or Decware, you will get amazing sound quality...liquid, full mid-range with no sacrifices in terms of bass. FYI, I enjoyed my Sennheiser HD650s much more out of my Singlepower Extreme, an OTL tube amp, than out of my Luxman P1-u, one of the best solid state amps on the market with a retail price of $3,000.
So for high impedance cans, go with an OTL, as their performance is amazing and they are often less expensive than transformer-coupled amps. If, on the other hand, you plan to switch to low impedance cans from Grado, Audeze, or JH Audio IEMs, a transformer-coupled tube amp or a solid state amp would be a better choice.
I realized after the fact that my new Kavent preamp has no headphone output...oops...so I bought a Bravo V2 because it's looks so cool (hasn't arrived yet so I have no idea what it sounds like). It's so inexpensive I figured how could I miss?...but am curious if anybody out there uses one. The Kavent has an extra set of line outs to drive it.
K den...the Bravo V2 arrived...and it's really a cool little bugger...sounds great on initial listening and is now the coolest looking thing in my "audio pile". Dead quiet and works perfectly using the unused single ended outputs on my preamp. BRAVO indeed! Cost less than 3 drinks in a New York bar.