Fairly new to streaming. Where to start?

$2k & under budget

Aralic Vega has streamer  and DAC. May be the easiest start?
Then there is Schiit...Yiggy or Gumby...which streamer?
Ladder NOS dac? Or Chip? I'm old. maybe I'll like the old school DAC?
Then there is  Benchmark DAC 3...I think it has streamer?
Exasound E32
Audio Mirror?
MHDT Orchid
Border Patrol?
Musical Paradise?
Whats a newbie to do? I am a classic rock fan with lots of FLAC & M4a files. I like detail & PRaT. Love a good bass line. I also play some 70's jazz. I have a Theta Miles CD player from the 1900's & play a lot of vinyl too. But I need to come into the 21st century.  Besides, I will probably become tired of the vinyl ritual and work at some point as I get older. I think I have done enough homework to be somewhat confused. Maybe the biggest question in light of how fast digital changes is the question of streamer with DAC or separate Streamer and DAC. One other question is the streamer & bridge the same thing? OK Thanks!! 
I'm going to give my Node2i to my son, so I will also be looking for a streamer only upgrade. I would prefer to use a separate DAC, perhaps Orchid.
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So, I have learned somethings and I'd thought I'd post. The Hans Beekhuysen book was a helpful primer on digital audio, but the real proof came with the purchase of a reclocker. I bought a Musical Fidelity X-DACv3 a couple of weekends ago because it matched the rest of my Musical Fidelity office system. The X-DAC didn't have USB so first I used a HDMI splitter to run the digital signal from my 2016 MacBookPro to the dac. Sounded ok. Then I ordered a Schiit Eitr reclocker off of ebay to push the digital signal into the dac, and sound improvement was drastically improved.

So, in conclusion, a iPhone may be able to play a FLAC and the pink light on an AQ Dragonfly Red lights up indicating that MQA files from Tidal are playing from your iPhone, but the sound you get is not nearly as good as a well clocked digital signal.

So my new question is: Would a fancy digital streamer sound better than an iPhone pushing its digital signal through a good reclocker?