[Dicetrain]

I have an HRT Music Streamer II+ feeding a Schiit Asgard that I plug some Grado 325is into. When I do this it is wonderfully balanced and smooth audio.
 
I also have the Grado adapter to turn it to a stereo jack. I tried to use this to extend the cord a bit, and used a 1/4 to 3.5 adapter to be able to plug it into the amp. When I did this it sounded like crap. The bass was muddy, the mids had unbalanced volume and shrill high notes would sometimes painfully peak in my ears. It made a lot of songs hard to listen to unless I really turned the volume down. Now, I assume since the Grado cables are made of the same stuff, that this just means the adapter is a piece of crap (I don't even remember how I got it) but I also wonder if it is just a problem with adapting from 1/4 to 3.5 to 1/4 again.
 
Anyway, the reason this is an issue is that I have some Swan M200 MkIII speakers. I have premium RCA cables connecting my DAC to my amp but that leaves these speakers out of the equation. The cables are a nice tight fit, but I don't want to be switching them out from my amp to my speakers all the time and wear down the cables or the ports. I do have a L/R RCA to stereo 3.5 cable of the same quality, so with an adapter I could plug this from my speakers into my amp. Sooo...
 
1) I have no idea if conversion of formats inherently degrades quality
2) If it doesn't, I could use a 1/4 to 3.5 adapter to plug my speakers into my amp, and would then need to know a good brand for such adapter, since via my headphones I found out the one I have is garbage.
3) My speakers are actually active desktop loudspeakers and have a unique system for it that won them awards and whatnot, so it may be better to just feed them directly from the DAC, which would require splitting the RCA from the DAC so I can have my speakers and amp plugged in at the same time. I am also clueless as to whether or not splitting inherently degrades quality, and if it doesn't I would be clueless about good brands for splitters.
 
If you are knowledgeable about these things please help and thank you ahead of time.

 

[65535]

For starters, adapting connectors with good quality undamaged adapters will not affect the signal noticeably. 
 
I'm slightly confused by your setup.
 
Plugging multiple devices into a single output isn't terrible as long as the input impedance is similar, though I personally like to avoid doing that if at all possible. If you got a splitter find something that is transformer based.