Upgrade guidance

Hello guys, I’ve been thinking about the best path for me to upgrade my audio set up.

I currently use a magni/modi stack with an old pair of AKG k701s. While I enjoy the k701s for listening to music and for competitive gaming, I think its time for a second pair of headphones. I don’t play competitive fps as often anymore and enjoy more coop games and story rich games.

I have been looking into the DT1990s and the HD660S, but I was wondering if anyone else has any suggestions. Im looking for more bass than the k701s, something warmer(?) but retains the detail and soundstage.

Also, in terms of upgrading my audio set up, it should be headphones first, amp, then DAC right? Would also appreciate it if you have any suggestions for upgrading my AMP/DAC setup.

Thank you!