Time to get up to speed (somewhat) with digital.

Looking to start using my Macbook Air for music.  I was going to just buy a 3.5mm to rca cable to start off but from what I've read this is not great for SQ.  So now considering a DAC.  Looking at used local choices of Benchmark 1 HDR, Jolida Glass FX, McCormack DAC 1, or Hegel HD12.  The Hegel seems to be the newest and most versatile, but also the most expensive.  Not looking to break the bank, but also don't want something that is already outdated.  Then there is the Dragonfly at the low end of the budget.  

Just starting to educate myself on this topic.  I've been happy with CDs for a long time and my fairly recent TT purchase.  But realize I am missing out on a whole lot of music out there!   

FYI current preamps only have RCA connections. 

Any knowledge/opinions appreciated!  
Does your Air have a usb out? That's the way to go but if you use Audrivana then you might not have enough processing speed. If it's just iTunes then you should be okay. Not sure if it does but I use my MAcBook Pro into an RME-ADI-2 DAC. Superb results! Check out the RME though.
Yes, two USB out.  Also has a Thunderbolt port.  It's an older computer.  I will take a look at the RME.

I like my Dragonfly Black but there is also the Red and the new Cobalt. All of them has gotten good reviews. I think you coild be happy wirh anyone of them for tears to come.

You can also try Ifi nano black or one of their more expensive versions.
for great DAC's at reasonable prices take a look at Schiit Audio. they have something for all budgets, upgradable as well. 

I also would like to start getting into Hi Rez digital music files. I'm seriously considering purchasing the Audio-gd R28 Dac/amp
I like the fact that I can connect my Oppo BD 105 via balanced XRL connections to the R28 and then connect via balanced XRL to my old school ARC LS15 pre amp, which in turn is connected to my VAC PA 80 80  The build quality of the R28 is top notch for the price ($1,250 ish) shipped and the sound quality is also top notch