If you had to start all over again in this day and age

Interesting question to ponder. 
Life is a journey and I like my current system. I also have all the music I have ever bought - vinyl, tape, CD and digital with the exception of albums stolen while in college. 
Streaming is awesome and a great way to get exposed to different music by other music lovers...

I would not change a thing in my system. I am very pleased with my speaker and headphone setups. 

I would not start at all.

Of course, there would be something to listen to. A nice Walkman with decent earphones and $100-200 Bluetooth speaker. iPod Touch for Internet radio. Which is what I mostly use these days anyway. All the music I have fits on microSD card. In Walkman and in the car.

Just did this process after downsizing. I sold my Passlabs X-250 and am selling my AR Ref 1...couldn’t fit these components in a new BDR cabinet and couldn’t expose the new grand baby to the heat!. I chose the Gold Note IS-1000 Deluxe which is in my opinion a beautiful piece with integrated amp, phono stage, upgraded DAC, and excellent streaming capability. I am very happy with the level of performance and versatility. I kept my Vienna Acoustic Mahler speakers, and Teres Audio turntable rig. I love my vinyl but am not opposed to entering the hi-Rez streaming world either...