If you have zero aftermarket cables, that would be where I'd start for the biggest bang for the buck. Having just been through a sincere upgrade in cables about 5 years ago, it began with the Darwin Silver IC's. I'd had several good for the money cables like Morrow, Crimson, DNM, Audioquest, Magnan, that were all nice sounding cables and a noticeable upgrade from standard cables, but the Darwin's opened my ears as to what was possible at a similar price. Their cables got progressively more expensive the past couple years, but were also better sounding as they came out with new cables that were more expensive. BUT...the Darwin Silver would get you much closer to what you want at a very reasonable price--under $175 per IC pair. It would leave you with enough to buy a couple nice power cables and maybe even some good speaker cables. You could find some used WyWires Juice II PCs for under $250 per. If the speakers you have are what you really like short of their dynamics and low bass, the sub would be a good idea. If you did the ICs I mention, added a power cord or 2, and got a nice sub, you'd think you'd died and gone to heaven compared to what you have now. Other than speakers that don't do low and a total lack of good cables, your system is a nice collection of components. The cabling would be the single biggest change you could make.
The components in my system have remained relatively unchanged for the last 4-5 years, but I've upgraded most of my cables in all categories considerably again. I've also done much tweaking to almost all areas mostly with great results. This has been done with both analog and digital.
PM me for more detailed info.
Bob