I would continue to work on your room.
Looking over your equipment. I would say, given what you have said, Bryson is probably not a good match for your tastes (or mine). While quiet and detailed, they are pretty analytical and the opposite of sweet and musical.
While upgrading your DAC will gain you a lot. I think the first thing you want is to get your central components correct to your tastes (preamp and Amp). I think you would be much happier with a tubed preamp (as high a quality as you can afford)… and a warmer amp… since your speakers are 88db… not tremendously efficient, you will probably have to use a solid state amp (tube would be preferred, but I am guessing a good 60wpc tube amp is not in your budget)… you want a warm amp… things like Krell, Pass, and CJ come to mind… probably above your budget. Some folks hear can probably recommend some lower budget options.