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

Would keep all my kit. Moon by Simaudio 390 streaming Pre. Moon 330A, Rega RP8, Raven Audio CeLest Towers and all Raven Cables.

I would do what Kren0006 suggested. 
I'm almost to retirement, and I just got my first streamer and HI res streaming service.  Now I wonder why I waited so long!  I can get music however I want it: Playlists, albums, genres, etc. 
Half your money on speakers, half on the rest. ...ish...

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.