"Lossless" is a bit unlucky. "Bit perfect" is where this is about. Android by design resamples all audio to 48 kHz. In the past there were media players allowing you to bypass this default sample rate (and therefore the entire android audio) using a USB DAC. This now has become an option in...

Try this one: https://www.head-fi.org/threads/headphone-amp-impedance-questions-find-the-answers-here.607282/

Have a look here: https://www.audiosciencereview.com/forum/index.php?threads/eq-software-for-windows-linux-macos-ios-ipados-and-android.18450/

As bit perfect means no alteration of the number of channels, the samples and the sample rate, it is most of all a impossible question as you can't do EQ without altering the samples. EQ is bit imperfect by design and when done right, sound quality improves compared with a bit perfect stream.

https://rme-audio.de/adi-2-4-pro-se.html

If we assume identical amps, it will be worse! Using 2 amps instead of one will double the power double the distortion double the impedance However, well designed amps have such a low distortion and impedance, this doubling is trivial. In practice the single ended might be substantial worse spec...

There is an exception to this rule. The Pentaconn is TRRRS so 2x2 for the "balanced" connection and a ground. This can be used for TRS connection by using L+, R+ and the Ground.

Wouldn't be surprised if you can install a UPnP compliant media server on it. If your "homeserver" is a NAS e.g. Synology or Qnap, it even comes with one. PS: https://support.plex.tv/articles/200350536-dlna/ says plex support DLNA so you can combine it with a WiiM

Try https://diyaudioheaven.wordpress.com/digital/pc-software/foobar-2000-for-dummies-part-3-new-experimental-sacd-plugin-v-0-9-x/

Don't know if it is still available but Sound Liaison did offer one in 768: https://www.audiosciencereview.com/forum/index.php?threads/finally-music-we-can-buy-in-768-khz-sampling-rates.29544/#post-1033369 If not, you have to settle for 24/352...

Tagging WAV is a known problem. The WAV tagging standard is a bit limited (no album art). Some developers solve this by writing ID3 tags to WAV but that is not a standard. https://www.thewelltemperedcomputer.com/KB/WAV_KB.htm My suggestion would be to convert some files to FLAC. Check the FLACs...

Best is an amp like the A50s. You can choose between high and low gain (less power). The low setting is ideal for IEMs as they are often high sensitivity.

As the N100 is a transport only and delivers USB audio, you might decide to add a DSP module doing the EQ https://www.audiosciencereview.com/forum/index.php?threads/using-orangepi-zero2-as-an-equalizer-between-usb-source-and-usb-dac.53750/#post-1946851

To the best of my knowledge, Tidal Exclusive uses WASAPI in Exclusive mode so it talks straight to the DAC and can do automatic sample rate switching. In fact the whole Win audio is bypassed. Wonder why you use Voicemeeter.

The Jotunheim 2 can be found here: https://www.audiosciencereview.com/forum/index.php?threads/schiit-jotunheim-2-review-dac-headphone-amp.21232/ Wouldn't go for the multibit DAC, way to noisy. It has analog balanced in and outputs at line level and a "balanced" headphone out. Personally I'm not...