Why did you choose the components and speakers that are in your system?

In my current system, the TT was the inspiration for upgrading the whole thing. After looking for many years for a cherry rebuilt Garrard 301, I found a beautiful one built by Woodsong Audio. Being of very high quality, I upped my entire system to match.
That was a unique case. Mostly, speakers are the best component in which to base a system. Match a proper amp, preamp (or integrated), cables, power, vibration control and source.

I focused on the system and the room and specifically how I wanted to use it.

When I started to build my system I decided on a 2 channel stereo system in the living room in order to encourage conversation - no TV.

And then I created a budget and based on my personal experience and taste decided in building using a NAD integrated receiver and chose speakers that I felt produced the best sound (Sonus faber was selected over B&W and PSB).

The system was analogy (turntable, tuner and tapedeck), I added a DAC/streamer.

When I upgraded - I started with a separate pre-amp to improve the DAC and phono stage.  Then I upgraded the amp and then improved the sources and the speakers.

In retrospect the best thing I did was establish a budget and identify my goals and then enjoy the system.

If I was given an opportunity to start over from scratch again.  I'd build off my current speakers (Sonus faber Olympica Nova V) and turntable (Rega P8) and evaluate amplification, phono stage and DAC.  I currently have McIntosh amps and Moon by Simaudio DAC/Streamer and I'd add Audio Research into the audition mix. 

The lesson I learned is the value of cables.  And the value of cables is dependent on the system and I noticed significant improvements in details and clarity when upgrading from what I would consider value priced items to 'specialized products' where the product design and production are core competencies of the company.  Some may say its snake oil - I heard and liked the differences and would encourage experimenting before dismissing the idea.

Cost/benefit ratio.

IMO, Other than DIY, highest was speakers (pairs of Quad 2905's); lowest was cables. Still haven't spent enough to justify cables better than those based on Canare Starquad microphone cable. Maybe after the second Koetsu I'll take another look  ...  YMMV

Can you setup Open Baffle speakers in your listening area?
They need to be 5-6 feet into a room. Conventional speakers 2-3 Feet.

If your current speakers have 6-8" woofers and have the room size required you might get the Spatial 15" open baffle speakers and really
appreciate the difference.

Or as suggested try some electrostatic or planars

Furman 20 PFI - protection + clean power without loss of dynamics
Airport Express - to transfer data only (computer not important)
Benchmark DAC3 HGC - to make 280ps of AE jitter inaudible.
Benchmark AHB2 - very clean and very dynamic.
Hyperion HPS-938 - Giant killer speakers.