As far as your monitors, or any sub$1000/pair monitors, I am doubtful that you will find satisfaction with that route. I never upped my game to the $1000 monitors, but used a couple different approx $700/pair monitors and never got what I considered to be realistic piano sound reproduction. I have heard reports from reliable members here and on another forum that above $1000 the monitors are pleasing. i don't know for myself.
First, let me say that, with the exception of DACs, all my equipment has been purchased "used". I get more bang for the buck, and believe me, the bucks can disappear fast in the hifi world.
I am firmly in the hifi camp when it comes to playing your digital piano or VSTs. My path has gone through, in order, a Pioneer 5.1 home theater receiver, a Denon 5.1 home theater receiver, and now, an Adcom class A-B amp. Each was better than those before it. Particularly, the jump from home theater receiver to a music focused amp like the Adcom (or NAD) was the biggest jump in sound quality. These amps are far better at producing a warm, woody sound from piano recordings/VSTs.
As for speakers, they have proven that you just don't know what you don't know. I've had cheap, and thought they were good. Until, I heard better. At one point i purchased a set of Energy Towers (each with dual 6.5" drivers) and thought i was in heaven. Their MSRP was about $1400/pr., but ended up with a street price of about $700/pr. But, along the way, I discovered better, and bought better. The best speakers i have had, my current ones, are just a pair of dual 6.5s in the form of a kit from Parts Express. The kit was about $400, but I bought them used from the kit builder for $90.
There are bargains to be had in the used market if you are willing to invest your time in familiarizing yourself with what if available, and what is possible.
My current setup sounds very nice playing piano recordings and reproducing piano sounds from VSTs. It consists of:
Topping D50s DAC (purchased new for $200);
BSR 10 Band, 2 Channel equalizer ($10 used);
ADCOM GFA-535II amp ($180 used)
Parts Express $400 speaker kit with dual 6.5" drivers ($90).
So, you can get into nice sound from relatively few dollars if you take your time and keep your eyes open for bargains.
Good luck to you!