Okay if you're saying this is possible I'm willing to get anything required and leave it at home for the DAC and when I'm out just use the amp just as long as it doesn't cost too much.
Is this the combo I need?
http://www.ebay.com/itm/6-in-1-HDMI-Dock-Adapter-AV-USB-Cable-Camera-Connection-Kit-for-iPad-iPhone-DZ88-/131079147710
+
http://www.ebay.com/itm/One-Black-Dock-Extender-Adapter-for-iPhone-5-5S-5C-Fit-Lifeproof-Otterbox-Case-/111297991898?pt=US_Cell_Phone_PDA_Cables_Adapters&hash=item19e9e094da
I wouldn't know if those will work as I've only used - and observed as working - the
original Camera Connection Kit. If anything, try to get that dock extender, as I assume it will be something necessary for using with your phone's case, instead of paying the full $30 for the converter. However, if you're willing to risk the $13, might as well get that generic CCK too as it has a lineout connection, and you can try that out with a 3.5mm to 3.5mm cable going to an amp's analog input.
Do the adaptor + cck have a chance of ruining the amp's potential?
Either it will work with a digital output into a DAC(-HPamp), or a fixed analog lineout,* or it wouldn't. Don't sweat details about the sound getting ruined by more components, considering that if it
does work either way, the device doesn't work otherwise, so there's no basis for comparison using the same device. Don't think of this in the same way as, for example, a true DAC unit with a neutral discrete or HDAM output stage and then putting tube buffers or whatever between it and the (pre)amp.
*which I can't make any guesses to the affirmative because I can't be sure how Lightning will work with an adapter, considering the original Apple dock has a DAC chip wired inside it to provide a line out signal
Do you mean if it wasn't used as a transportable it would make sense?
Portable - DAP or device used as digital transport strapped to an HPamp or DAC-HPamp, used on the go; if it's a smartphone, you won't be using a headset through the amp, so when you answer the phone, you bring the phone, amp, DAC (the whole shebang) up to your mouth
Transportable - DAP or device used as digital transport in your pocket or one bag compartment, and other related components like an amp and maybe a DAC in their own bag or a compartment in whatever bag you have, to be assembled together as a system when you get to a location where you are likely to spend an extended period of time, like at home and then transported to the office or a hotel room
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So what I meant was all the clumsy adapters and an amp, maybe with a DAC built in (even if it's battery powered), would be more easily used stashed neatly in a bag then assembled on site like when Rangers take pack howitzers that can be taken apart and and the separate pieces carried by the gunnery crew, compared to bringing that whole shebang strapped together and any movement can dislodge the adaptors or you have to lift the whole rig to your lips when a call comes through. Again, the problem here is that Lightning requires adapters for the Apple CCK, and while there are some generic Lightning CCKs available, your case presumably needs an extender. Given you are sticking with the K550, you can always just use the stock Apple earbuds or get cheap but considerably better earbuds on the go, then when settled down set up the transportable kit.
That or if you're willing to divorce iTunes for music management you can get a one-box DAP like the Ibasso DX50, which has a proper DAC circuit with an output stage that feeds a good enough power amp section in it. Note that this will be a paradigm shift, which is why I did not take this up earlier, since you won't be using iTunes, something that historically has been kind of a traumatic experience for iDevice users, and that's before the beta firmware woes on early buyers. For example I know someone who tried using my old iPod with a Rockbox firmaware and she had no idea what the heck drag and drop is despite the fact that she uses a USB drive for work.