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

Started from scratch again, building my fifth system in 60 years.  To enjoy great music, I started with a pair of ACT SRC50's-active, and PS Audio electronics from the regenerator (great), direct stream DAC, direct stream transport, BHK preamp (Amprex inside) and excellent interconnects by Vertre.  It's a simple system, not one that fills the room with hardware, and totally enjoyable.  Next step is a Innous Zenith MkIII, and maybe a pair of REL subs.  I have used a myriad of great equipment in the past and I think I have bettered all of it.  BTW, I got out of vinyl because of the constant tinkering and "tics".  Took too much time away from listening to great music.

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.