Help a Newb To Streaming Set up a Streamer and Simplify his Set up

Would appreciate any advice for a streaming rookie to simplify and neaten my set up in my home office.  

My current set up for music is to use my desktop iMac with Audivarna out to a portable Ifi amp/dac placed on my actual desk. I than run a 25 foot pair of ICs out from the dac to my pre amp and stereo set up on the other side of the room. I like this set up because, i can control my music selections and volume while I'm working on the cpu and have the option to plug in a good set of headphones at my desk when the speaker volume will disturb the rest of the house.  

The drawback is i have to run outrightly cables across the room and cant remove the Iifi and use the amp/dac in other parts of the house since its designed to be semi portable. 

So i would like to set up a streamer and permanent dac on my audio rack on the other side of the room, preferably controlled by the iMac rather than reaching for my phone or tablet to control the audio system.  This is because i like the sound of audivarna. I primarily stream Tidal but would also like the option to plug in usb hard drive to the streamer to play my collection of hard drive stored live music. 

However if i do this i would lose the ability to plug in my headphones unless i run a headphone cable back across the room. 

So what should i explore? Do i want a streamer that can be controlled wireless by audiovarna? I see the new version of audivana uses UPnP, but I'm not sure exactly what this does but will that allow me to control the streamer from the cpu?

Or do i need something like a Sonare microrendu? Also not sure what this does, but will that act as a streamer or just an interface to the network and i still need a player/renderer? I do have a router near my audio rack which could plug into the streamer if need be, but don't know if this is necessary. 

Also is there a recommended way to keep the headphone function on the desk? Or should i just buy say a inexpensive dac/amp like a firefly or Schidtt and leave it on the desk?

Its hard to provide budget at this point because I'm not really sure what would be a decent way to proceed….but would like to separate a new DAC from the streamer so i can upgrade or change later if necessary.

thanks for any suggestions or recommendations.
I don’t know if this is useful since your requirements are specific and don’t match mine exactly but here’s the setup that works well for me.

All my music is on the internal hard drive of an iMac in my office and managed with iTunes, mostly AIFF and Apple Lossless with a fair number of mp3s, as well. From the iMac I can listen to systems in my office, living room and garage simultaneously.

For the main system in the living room, the music is streamed from the iMac over WiFi to an Apple Extreme router and connected to an Arcam rPlay streamer with an Ethernet cable. The rPlay has an internal DAC but I use its digital coax output to go to a Wyred4Sound DAC with analog output to my integrated amp. The rPlay will accept the WiFi signal directly but since my router is just a few feet away I use the Ethernet connection simply for reliability, though I’ve never had any issues with my WiFi setup.

Before I got the rPlay I was streaming to an Apple TV and using its optical output to the DAC but the new setup sounds dramatically better, as good as music from a Simaudio CD player connected directly to the other coax input in the DAC.

The rPlay will handle streaming from Tidal, Qobuz and other sources but I stream only Spotify at the moment. I’m extremely pleased with its simplicity, sonic quality and cost effectiveness.,rSeries,Music-Streamer,rPlay.htm