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

OMG  - what would I change in 2020 vs. what I listened to 10, 20 or 30 years ago? That is too easy - streaming is the future - I have been using a LUMIN D1 for 5 years. This gave me access to new sources of music beyond my ‘ear drums’ could ever dream of!!! Music is the reason for this hobby! Tidal Hi Fi with MQA is the best. Solid state integrated amps solve multiple problems (I am a Krell guy), Speakers are personal taste and room dependent - a Maggie guy for 30 years. Just bring enough power and enjoy the music!! You want more bass - add a Maggie bass panel and bi-amp it. Just upgraded to the LUMIN T2 - OMG - the sound stage - the detail - the vocals are amazing! 

Streaming is the future!

enjoy the music - Happy Listening!

Tom8999

Hegel 390
Magnepan 1.7s, Fritz 2 Ways,
or powered Elac Navis with a preamp/streamer/Dac. 
Innuos Streamer
Kimber Cables
Dedicated Power
No LPs, Cds or DVDs
All in for $10k.

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...