Best route to go for new dac?

I was in the same boat a few months ago.  I was also using a red dragonfly with jitterbug.

I ended up with a Schiit Gungir multibit, used for $850.  I would recommend some schiit dac or the mhdt.  Schiit is built in CA and their dacs are modular so you can upgrade them.  
There is a Schiit Bifrost for sale local to me.  It is the older chipset, called uber, not the newer multibit. You can upgrade it to multibit if you wanted to.  He’s selling it with an asgard 2 headphone amp at a good price.  PM if you want more info!

I use a Macbook Pro running Amara Luxe to a Schist Yggdrasil GS. The Yaggie GS at $1599 is the greatest steal in audio, in my opinion. First time in my system (Audio Research SP6B + C-J MV75A-1 or GAS Ampzilla driving ATC SCM 35's) that I have felt digital is superior to analogue (Benz Ace on a Grace 707 and Ariston RD-11s). So much sheer drive to the music, with incredible detail and 3-dimensional body without the dry, grainy whitish highs of my previous digital setups.

Check out the Jolida/Black Ice tube DAC.