If I understand your setup. I would start with an upgrade to your DAC. I have lived with a Sim Moon 760? For many years… it lacked natural / musical sound. So I would definitely start there. Then you want a good streamer… of equal cost to the DAC… I am a real fan of Aurrender.
My experience of upgrading and trying to get digital to the level of analog over the last 35 plus years is that today an appropriate approximate investment level is stand alone streamer = DAC = preamp = amp. They must be carefully chosen to be of the sound type you like (detailed and fatiguing vs musical and natural) and compatible.
So I would first calculate what you should spend on the DAC and then get that first… then a streamer. I’ve used Roon, seems like a very unnecessary complication to me… but some folks like it.