I hate answers like this, but, it depends! I've been doing some upgrading over the last year. I started the upgrade process with some pretty good speakers (magneplanar 1.6 QR) that I was ready to sell because my system sounded pretty awful. Thinking through a few questions before I started helped me significantly improve my system without overspending.
Q1. What don't I like about the current sound?
Answer: Digital glare, grain, weak bass, room resonances, poor soundstage.
Q2. What is causing what I don't like?
Answer: Digital glare--CD Player, grain-- cables and amp, weak base--amp, room resonances-- corners that needed treatment, poor stoundstage-- CDP, room, and speaker placement.
Q3. I've got a lot to upgrade, what's the biggest bang for the buck?
Answer in order of impact:
#1 Room treatment for $100 made a huge difference
#2 new DAC
#3 amp
#4 cables
The learning points for me were
1. Good speakers + bad supporting equipment & room = bad sound
2. Be patient. Try to identify weak links in the system. Upgrade one thing at a time, understand if the change fixed the perceived problem before making the next sysmtem change.
3. Look for well reviewed/high resale value equipment. This allows you to experiment and resell if your equipment if the change doesn't address the problems.
4. Have fun and enjoy the music!