FIrst of all, thank you so much for all the kind help and taking the time to respond! Each of you make me want to follow your advice! Responses below, fwiw.
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I would say to get the FiiO X3 or X1 and use low impedance headphones with it, so you will not need to buy a separate amp or dac/amp.
I've been really enjoying my Audio Technica ATH-ESW9 (there is also the ATH-ESW9A model).
Yeah, this is definitely the easiest solution. I'm concerned the X3 will be too dark, but I haven't heard one yet. Do you you like the X3 w/ the HD558? I just picked up a pair for casual around the house listening... On the other hand, the X3 would go great with the ER4S.
I would buy the phone you want, making sure that the model you choose has some method for digital out. At that point there are a ton of portable dac's/amps to choose from, and you get the flexibility to choose both the phone you want and the dac/amp you want and can update them independently.
I'm really tempted by this option. Unfortunately, I'm looking for an off contract, budget phone that could handle at least 64gb sd card and has digital out. They're out there, but the options are limited on a budget. On the other hand, there are sooo many really good dac/amps now that it does seem like a really good solution. If I get a portable dac/amp, I could use it with my laptop, tablet, etc. too (provided there is a digital out).
Funny I just sold my ipod 5th gen touch and could not be happier. My HRT microstreamer has never sounded as good as it does now with an android phone (Moto X) . Nice step up from the ipod and the touch was a big step up form any of the hard drive ipods I had.
I think a good used Sammy S4 and the HRT would be a good phone dac, amp combo. Or you could do a cheap tablet. I am going to be doing that for home bedside use. Researched the crap out of new models and the Lenovo Tab S8 looks to be a nice choice for me at $199. I'll be buying it as soon as they release it. Good luck in your search.
Great to hear you like the microstreamer for this kind of purpose! So glad to hear it was an improvement over ipods; I was really regrettin my decision. I'm kind of more in the Moto G budget, but I read that it has a digital out. I have started looking at used Samsung phones.. I really haven't considered a tablet but I have a Nexus 7, though I'd need one that has a SD slot. Do you know if the Tab S8 will have a digital out? Personally, I'd love to find a tablet that has a user-replaceable batter with a SD slot; that would seem to be the best of both worlds. Its one of the things I like about the Samsung phones.
What's wrong with the amps on those? They're still a heck of a lot better than CMOYs. I had the X3 in a crowded showroom and the Q701's bass was still audible (not to mention tight but had a deep response) - everything else was, up to that point, woudl have been surprising for me for $200 (considering the old D4 Mamba and the previous D2 both had trouble driving the HD600 and K701). Also if you're using an IEM even an iPhone can do well enough considering their efficiency (and the flat response on the iPhone - which is a lot better than my T-Mobile S3, which sounds a bit dark).
If you're using full-size headphones I suggest low impedance cans that don't need a lot of current (high efficiency, impedance stays near nominal during dynamic peaks, etc). Or maybe skip the portable player if the system is mostly for your home, then use a dedicated music server; or a smartphone that can function as a music server with a DAC(+HPamp) at home and then fairly efficient IEMs on the go.
I haven't heard either the X1 or X3; I've only read some criticize the amp as the weakest part of overall excellent daps and not up to the level of the dac's potential. I see lot of amps strapped to them which seems to defeat a little of the purpose. Unfortunately, I have a soft-spot for the ER4S, which at 100 ohms, requires more of the juice of the X3 than the ipod, though it isn't horrible straight out of an ipod.
My at home headphones are the HD558 which shouldn't be too hard to drive, but realistically far more of my listneing will be either on the ER4S or W40. Just got a great deal on the W40, though not sure I'll be keeping them. The W4 always sounded a little muddy in the mid-bass though it is technically brilliant. But the W40 is fairly efficient. I do like your idea of maybe just getting a great sounding smartphone. Or honestly, for 30% of my listening, even really decent woudl be ok. Maybe I should just look for a great sounding smartphone...