Good news! Finally cracked it.

Just use VAC with VBAN and I'm good to go. All I need now is to tweak a few things regarding volume on my side, but it works perfectly on my bf's pc.

I'll come back and detail the solution later for reference in case there is any other crazy out there like me.

Thank you for your response.

Music sharing is just so frustrating. I don't want to "dj" (ie: mix) tracks, I don't want voiceovers, jingles, adverts. I just want to synchronously share my playlist in my own home. And I certainly don't want to upload my music to a site and then work to configure my firewall to not broadcast it. >.<

I looked up Shoutcast and Icecast. The free versions don't seem to handle FLAC. But it did point me to jargon, so I re-Googled and came up with a bunch of "radio" programs - all too fully featured and bloated for my use.

I did manage to come up with a number of articles for whole-home music... but they all assume speakers.

I'm going to keep digging, but it looks like the answer is another >200$ headset from Sennheiser that will share the signal that then my bf won't want to wear. My ex always teased me when I tried to show him tools that would "assist/modernize" the creation of his drawings... always took 2 to 5 times longer than him doing the work (re-tracing, copying and/or screening) by hand. I feel like like I'm back there again in time:

"Hey, let's listen to my computerized playlist together!"
Days later...
"Nvmd ~~~~~ idontwanttotalkaboutit"

>.< Life. What do? >.<

MediaMonkey itself can't do this. Shoutcast/Icecast used to be available for this, they may still be.

I've searched for the answer, but I just don't seem to know the correct key words - so I'm not dialing in answers. I'm hoping you all can point me in the correct direction.

What I want: I want to be on my computer, launch my playlist, and have my bf on his computer be able to "tune into it". Basically, we listen to music at night, and we can't be blasting a speaker, so I want to host my own local radio that we can listen to communally over our individual rigs.

Is this possible?

T.I.A.