Start with Upgrade to DAC?

I am ready to set out on an upgrade cycle to my system, which consists of the following, over the next couple of years:

* Rogue Audio RP-7 Preamp (Upgrades: Rogue RP-9 or McIntosh C2800--C2800 includes Phono preamp and DAC)

* Odyssey Kismet Monobloc Amplifiers (Keepers!)

* Lounge Audio LCR Gold phono preamp (Keeper!)

* Fyne Audio F-702 Speakers (Keepers!)

* Definitive Tech Supercube 6000 (Vandersteen Sub Three or Paradigm XR11)

* Schiit Bifrost 2/64 DAC (Schiit Yggydraseil or ????)

* NAD C568 CD Player used as transport (Schiit Urd or ???)

* iFi Zen Stream

*iPad Pro for Apple Music

* Ice Age Audio OFC Power Cords

* Audioquest and mostly Morrow Interconnects (RCA & XLR)

* Performance Audio Speaker Cables, using Mogami W3104 Speaker Wire

  I am thinking that perhaps the best place to start would be the DAC, with the idea of moving from the Bifrost 2/64, which I like, to the Yggdrasil (model TBD) DAC, which has gotten superb reviews that speak to sound quality characteristics that are of concern to me.  Budget for DAC upgrade is about $2500.  OR, should I go for room correction capability?

I recently replaced a highly-rated 100 wpc tube amplifier with the Odyssey mono blocs, and I was stunned by the improvement in sound quality, definition, and imaging, but I think there still is some room for improvement.

Thoughts and recommendations most welcome.